(I'm just kidding, I know you said you're only asking from the perspective of technical curiosity.)

That's a really tough question to answer. From my point of view, the short answer is yes...

The long answer involves all sorts of shit that you and everyone else would probably find incredibly boring. But, basically, I can see a path to eventually getting Bitcointalk to a place where the database remains as-is, but it's "wrapped" in a way that makes it possible for it to service multiple frontends. In that universe, there'd still be the tried-and-true "legacy" frontend for the diehards that want to keep using SMF, but there'd also be one or more "modern" frontends that would be more feature-rich and would be much easier to develop on (right now, adding features to the forum involves way more work/thinking than it really should: SMF is a security-incident minefield; a saner architecture/codebase would allow for development to happen at a much quicker pace). Another way to state my perspective is that I think SMF's database schema and invariants could be maintained (at least, to the extent that the "legacy" frontend wouldn't break), and that, with clever enough engineering, non-SMF frontends could be erected on top of the existing database, allowing a modernization effort to progress without ever actually having to "migrate" anything or anyone.

Yup, that would be nice! But, like Loyce mentioned, I can't imagine theymos wanting to deal with the hassle of hosting the images directly. I've been thinking for a while now about some kind of distributed image hosting, run on a volunteer-basis by interested forum members. I've also been thinking about a new BBCode tag to specifically reference content-addressable images that are being hosted in this way. If that project ever gets off the ground, then I can see a way to make uploading images feel like a completely built-in feature (but without getting theymos tangled in administrative/legal issues).