I don't know if I'd like that. As much as I love reading my own posts from way back, picking one over the others is always pretty hard, let alone five. But I agree, some posts are meant to be read for one day (or week) and then forgotten. Others are made to shine forever! It would be great to have something to keep them apart.
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I like the idea of editing the favourites and swapping them out though! I have always thought it was a good idea, even if I do say so myself!
You are pretty good at designing your posts with appealing looking footers, so you could have five thumbnails to each of your posts, linked to your current fave-fives (hey, that catchy term just popped into my head, but feel free to adopt it if you like it).