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The posts are stored in comments on the chain and there are lots of comment already. What would happen when we have like 1000 posts? I like the simple UI of the site, and how the post are displayed but what if I want my annonymous post to reach some set of people on the chain who are not using https://anonramblings.com at all?

I hear you, main posts is refreshed every day, so the comment count per day should be manageable. If people use it very much and post hundreds/thausonds of stuff every day then I agree with you. Then we can think a solution but I don't want to solve scalability problems of the future. :)

how about posting them to a community as posts

Doable. But there is a five min, one post restriction in main posts - which may create larger queues.

multiple accounts i.e confessions, whistle blower, advice etc. its easy to moderate posts