@tinyitx's summary is pretty spot on here - while it would be convenient for us to allow everyone to upload media onto SFF.N, the challenge is that when we provide that ability, we're committing to storing and serving those uploads for the lifetime of SFF.N. Furthermore, we can't really anticipate how much folks will want to upload to SFF.N, when given the ability - presumably even more than they'd put on Imgur or elsewhere otherwise. So if that was something anyone could do for free, we'd be committing to a perpetual cost that we couldn't really estimate. This is rather risky for us to take on.
SFF.N does run an image proxy - that is, we make copies of linked media files and host them locally for our most-visited posts/threads in order to improve performance - so we actually have some data with respect to the footprint and bandwidth demands that this content generates. It's a lot - gigabytes of new data each month, translating into terabytes of bandwidth usage. We like our photos here!
The compromise solution we've settled on to date is to allow supporters to upload media directly, because they're covering the cost of that benefit through their contributions. Right now, that is a Silver subscription benefit, but perhaps in the future that is something that could be brought down (at least in part) to Bronze supporters - we have planned enhancements and changes to our supporter subscriptions on top of the ones we've already rolled out in the past 12-18 months.
As for viewing post history - we have that capability enabled for staff and moderator accounts, but providing some form of it more consistently to users is an interesting idea, though I would bet folks would disagree on whether it's better to have it or not. I would say that our current implementation is really geared towards moderation duties, so if we were to introduce that sort of functionality we would want it to be a better experience that's more parseable to end users.