• I think most people should at least have a best guess about where they would donate if they hadn't participated in a lottery, and if it's easy then they should plausibly give a token amount directly (like 10%). This makes "give to lottery" much more comparable to "give directly" since you've still spent the time thinking about it, have your head in the game, and can talk from experience about that decision. (Another simple reason to do this is to confirm that actually diminishing returns aren't a big deal wherever you were planning to donate.)
• If someone really means to ask "where should I donate?" and "not where did you donate?" then it seems like you can just answer that question. Giving 10% to the object level makes that even easier but I feel like I can basically do that even when I don't give directly to the particular charity I'm discussing. (That said, I probably get asked this question much less than you and by a very different distribution of people.)
• I particularly like donor lotteries because I think they are one of the cleanest "wins" amongst all EA recommendations for small donors (though not one of the largest wins). I think it's really complicated to assess whether you should defer to EAs that you don't really know, but that there are great arguments that most donors would be better served by using a lottery. So I consider it one of the most legible ways to clearly demonstrate that EA is just better at donating than other communities (rather than merely having complex methodological disagreements).
• I think that donor lotteries seem better for the health of the community than having a bunch of small donors who have no option other than deferring to a centralized recommender (whose work they often can't check very thoroughly). It empowers more people to have meaningful influence over how charity is done. "Small donors should just defer to professionals" might be right but I don't think it's very legibly right, and it relies on a bunch of trust. In practice if you are donating $10-100k I think that a lot of that has to be social proof rather than having the time to dig into claims enough to reliably tell that GiveWell knows their stuff. And even if everyone defers to an evaluator, the form of accountability seems important and I'd prefer evaluators be accountable to 10x fewer donors with 10x more time. Relatedly, I think this makes it easier in practice to start a competitor and market to a smaller number of large donors based on quality product.
• I do think a significant fraction of people (especially in tech or finance) respond positively to the idea of donor lotteries, and having the option value to talk about the object level or lotteries based on the audience seems good. Again, I think this might differ because we are talking to different audiences in a different way. I also think that I'm more interested in weird stuff than you, so I'm maybe particularly willing to lose out on prospective donors who aren't willing to spend 30 minutes thinking about a plausible-looking but weird idea, or who can't handle expected value calculations. And in general I more want EA to be the kind of place that does weird but good stuff.
• I don't think that "lots of people are thinking about the allocation of EA funds" has made it that much easier to be a small donor. Which of those people am I supposed to defer to? Also, I qualitatively don't feel like the ratio of (money moved) vs (time spent thinking about allocation) is that much better than it was in 2016. I wouldn't be surprised if both of those have grown ~4x in parallel.
• I agree some lottery-winners give to the same kinds of things that they would have given to otherwise, but in the two cases where I have the most information it seems like the outcome was very different. (For several of these grants I think that giving smaller amounts would not have been an option.) It's also worth noting that most small donors give much worse than you, and for many of them it would be great if "spend more time to think" got them up to "defer to GiveWell."
• I'd guess that your earning to give situation was similar to a small lottery winner but not a large lottery winner, and if you donated somewhere without significant diminishing returns then I think it might have made sense to go to an even larger scale. (Right now I personally feel like it's pretty plausible that a philanthropist with a $10M budget should do a lottery with a big EA foundation up to a $100M budget, if they'd offer it, though I'd defer to funders and charities about what they think would make for a healthier ecosystem.)

I’m not sure that you’re making the wrong call, but I think it’s sort of weird/hypocritical to advertise EA by making donation choices that sacrifice altruistic impact in order to seem more normal.

Another effect is that I’d much rather evangelize EA to the kind of people who understand donor lotteries quickly.

Disclaimers:

1. Writing quickly about a complex topic I have many vague ideas about
2. I won the $500k donor lottery, and it has been a very emotional experience, I think I will be in a better position to evaluate this in ~5 years, I'm extremely biased

Even trying to take into account my strong bias, I'm strongly in favor of donor lotteries, here are my 2 cents:

I confirm that you do get negative reactions to the concept of a "donor lottery" from most people, but you get even more negative reactions when you tell people you're donating most of your income, as I'm sure you know better than me.
I would go with the advice in why you should give to a donor lottery

we recommend that most people still make direct donations with some fraction of their donation budget. You can put most of your donations towards the donor lottery, and use the rest to donate wherever you would have if there wasn’t a donor lottery.

I personally would recommend 50-50 for most people, but with high variance. I think it would heavily mitigate your points b) and c), and keep you informed enough about giving opportunities to provide useful advice.

You can still share with people your direct donations and I think you have roughly the same influence whether you donate X to an organization or 2X. You can mention the donor lottery only to people that might find it interesting or useful.

If with some research you have a good chance of identifying better donation opportunities than "give to GiveWell or EA Funds", I'd be excited for you to do that and write up your results [...] there were many fewer people working full time on how to allocate EA money

In my experience, there are now many funds and grantmakers to choose from! The problem moved one level up but it's still there.

An advantage of moving to the ~$500k scale is that it makes sense for me to ask people that seem knowledgeable and trustworthy to confirm whether a fund/evaluator is actually reliable. It actually turned out that one (of the many) probably wasn't at the time, and I definitely might have donated to it otherwise.

I also think that donating to GiveWell's "All grants fund" is probably just better than donating directly to one of the recommended charities, because GiveWell only funds particularly effective programs, and many top charities run many programs in many countries with various levels of cost-effectiveness. But I see many donors not making these kinds of considerations that I think they would make if they won a donor lottery.
Another way to say this: many EA donors, like silly me last year, do not give to GiveWell funds or EA Funds, maybe for reasons similar to your points b) and c).

When I was donating my last 10k last year I was reading things that made me doubt the optimality of GiveWell's recommendation (like this series). At that scale, it would have been hard to justify the time to investigate whether those claims have merit.

Some IMHO more serious downsides of the donor lottery:

1. Unilateralist's curse, especially for longtermist funding where many opportunities have sign uncertainty
2. Potentially a less representative distribution compared to a "free market" approach where small funders distribute money according to their values.
   e.g. if half of the funders care only about insect suffering and half care only about mental health, it might be better to allocate the funds accordingly, instead of having 100% insects or 100% mental health depending on who wins the lottery.
3. People might over update on the opinions of a random lottery winner, compared to a grantmaker that was selected meritocratically, or a funder that at least earned the money.
4. It might be treated by the winner like "monopoly money", without the moral seriousness of considering the thousands of lives it impacts.

Some serious advantages of winning the donor lottery:

1. It makes sense to verify that the fund/evaluator you would be donating to is actually reliable with much higher confidence and compare funds with each other. (A popular one probably wasn't until months or years ago)
2. It makes sense to go much deeper into EA and cause prioritization. e.g. How much should I care about animals, WELLBYs vs QALYs vs GiveWell moral weights, longtermism vs short-termism, population ethics in general, whether to fund research or proved interventions). This helps not just with allocating the donor lottery winnings, but with all future donations and career choices, and helps give much better donation advice to various friends.
   I learned basic concepts like "population ethics" and "theory of change" only after winning the lottery. I expect many donors to not be familiar with these basic topics and I am still learning a lot. Also, how to decide allocation across cause areas seems a very tricky question, sensitive to ethical questions that there is no consensus on.
3. Many reliable people, even at large funds, encourage funding diversity. Especially for opportunities in the $50k ~ $1M range, which might be too large for very small funders and too small for very large funders. There are professional grantmakers for these, but they have different opinions on where the marginal $100k should go (which I think is good!)
4. Despite the perception of abundant funding for EA orgs, many of their leaders still spend a significant amount of time fundraising, which has a large opportunity cost. If you can identify things that would have otherwise been funded by EA funds anyway, you can save them significant amounts of time.
5. Publishing a grantmaking report after winning a donor lottery allows you to signal-boost projects that you considered especially valuable, providing them with more reach even if funding-wise you would already cover their funding gap.
6. It could accelerate the career of potentially promising grantmakers, the correlation between grantmaking skill and grantmaking budget seems far from perfect. You could use the lottery funds to provide valuable experience to someone that one day might work for e.g. Schmidt Futures.
7. It would be easier to find opportunities for leverage, you influence donations less when losing but potentially more when winning. I did end up talking to way more people about EA (with mixed results).

I think the existing donor lotteries might have been too small for someone at your scale to appreciate the advantages, would you feel the same about a ~$10M donor lottery?

In my experience, explaining donor lotteries is actually pretty engaging to the right sort of person. And I expect that sort of person to be a good fit for EA.

You are/were an extremely prominent earning-to-giver (you and Julia have blogs; you guys have been profiled on news articles for your donations a number of times). I suspect the vast majority of EA donors are not in a position where they inspire more donations-by-casual-donors than the size of their own donations.

If with some research you have a good chance of identifying better donation opportunities than "give to GiveWell or EA Funds", I'd be excited for you to do that and write up your results. 

Interestingly I recently tried this (here). It led to some money moved but less than I hoped. I would encourage others to do the same but also to have low expectations that anyone will listen to them or care or donate differently, I don’t expect the community is that agile/ responsive to suggestions.

If fact the whole experience made me much more likely to enter a donor lotteries – I now have a long list of places I expect should be funded and no where near enough funds to give so I might as well enter the lottery and see if that helps solve the problem.

I think this post misses something: the impact of a donation is typically a nonlinear function of donation size. 

Specifically, a donation of (say)  $200,000 typically achieves more than 100x more impact than a donation of $2,000. 

Why?

Because with $200,000, a charity can take meaningful actions now, whereas with $2,000 the funds will likely sit in the charity's bank account until the charity has built up enough funds from other sources to use the money meaningfully.  

And money has a time value.

[EDIT: As Linch pointed out, not necessarily good reasons to not participate in a donor lottery]

I think there are two additional criteria for participation in a donor lottery [EDIT: assuming you are less comfortable with random/speculative impact]:

1) The average winner would do at least as good a job as you in selecting where to donate as if you hadn't participated.

It means their enormous time sink in investigating where to donate would yield donation options at least as good as those from your cursory investigation. That's a relatively low bar, but it's still there.

If you are unusually rational and conscientious with your giving (which includes most in the EA community), then there is a good chance your giving will be more effective than a less conscientious person, even if they spent substantially more time thinking about where to donate. I anticipate most EAs would be more likely to join a donor lottery with other EAs than a lottery with participants sampled from the general population. For a random person in the population, there is a good chance your "cursory" investigation is as good or better than their "detailed" investigation.

2) You share similar values on what is most important as the others in the donor lottery

Say I joined a donor lottery with three other people. They have different ideas of what is most beneficial to the world. For one, it is building monuments to Chtulu. For another, it is dyeing cats purple. And for the last one, it is increasing the number of shrubs in their neighborhood. Even if more time allows them to find the best giving opportunities for the things they care about, I see little additional value in a world with a higher concentration of Cthulhu monuments, purple cats, or neighborhood shrubbery.

There are also extra transaction costs in transferring money through an extra step, although that argument can also be made of regrantors like EA Funds and probably isn't a big enough deal to change what you should decide

I think you point to relevant tradeoffs here. I myself am currently testing a different scheme to determine my donation: let the public (or anyone interested in participating) decide collectively where to donate. I believe this might...

• improve the decision quality due to crowd-sourcing information and reducing any bias (moral or otherwise) that I might have
• encourage others to think about various causes and potentially make them donate more as well

The downside is probably that the total effort spent in this decision is larger than would I take it on my own...

My polls look like this, sometimes with a fixed total amount, sometimes with a total that increases with participation (to give an incentive). Typically around 100 people participate in it:

What do you think of this?