Two entries will be easier to do, and I think you'll get more entries that way. I'd find two but find it harder to find the third one with the under-50 reputation.
I also like the idea of celebrating when your reach 1,000 entries!
Hope you're kidding with the 'stuck' part. We are all willing participants!
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The "stuck" part was about if I made a change without asking. By asking for help I found that a lot of people said each week finding 2 was pretty easy, but the 3rd was much more challenging.
I had really wanted to do themed weeks, but the feedback was it would force people into categories they may not care about. So if I had done this they would have been stuck choosing to either skip a week or deal with curating a category they didn't care about.
So by asking it provided some really good feedback.