The flag will always be listed on the “Old Flagged Posts” page.
No. You’ll only be able to flag a post twice, once as off-topic/ inappropriate/ spam, and once for moderator attention. But you’ll usually only flag a post once (I only realised it was possible when looking into it for this)
Posts you have flagged will display a “you flagged this as inappropriate/ off-topic/ spam / for moderators” below them, but you don’t have any page to list them all unless you’re a moderator/ admin. You can’t see if your own posts have been flagged unless you’re a mod/ admin.
Yes I am wondering ideas like flagging leading to a private moderator comment thread, a request for pre-moderating my own comment to avoid penalties, more reasons for flagging, more engagement by moderators, etc.
IE. would Discourse be a good platform for that.
Thanks for your time I may return to this post in a few months with a more focused discussion.