I know I've made a journal like this before, but I seem to have removed it and I can't remember anything that was said in the comments. So now I post it again, when it is actually relevant!
Back when I established my roster of characters, I decided to age them realistically. Being a broke ass retail scrub means I can't afford to get art nearly often enough to really do anything with that decision. That's why I started attaching a date to almost every picture and story involving one of my "living" characters, so that I could do several pictures of any given character in their "current" state, but still allow them to age (because hey, that took place in 2009, even though I posted it in 2011!). My primary motivation was allowing Mary to stay tiny and cute forever without being effectively immortal, or to return to being tiny and cute if I decide to get art of her grown up. Which turned out to be a stupid-ass basis for a decision, because I only ever had her drawn once.
Anyhow, this suddenly became relevant again because I'm nearly finished with a short story involving Adrien, set when he was 15. Since he's old enough to drink now, I'd have to post that all-new story with a 2009 date stamp. Should I keep setting my new content 6 years in the past and pretend there isn't a massive gap in meaningful uploads, or should I adjust the timeline? The latter option would involve posting new dates on old uploads and just sort of moving everything into the present (so that Mary can be tiny and cute right now, instead of 6 years ago, in that one and only picture in which I had her drawn).
I already plan on tweaking personalities (and perhaps appearances), so there will be some degree of retroactive continuity whether or not I adjust the timeline (for example, Beth gets off on butt stuff now, she just doesn't like stretching). Basically, if I have one of my legacy characters drawn in the same general state of being in which they were drawn before, would you as my watchers prefer the date stamp to read 2009 or 2015? Which would make more sense?