I used to run gallery on the spacefem site, but as the years go on, it gets to be a pain. I have to worry about when to update it. I forget the admin password and have to go into the database to reset it. But since I have my own server, I just figured it's the right thing to do. and I don't have *tons* of photos anyway... it's secured, I show it to friends after road trips.
Recently I've been thinking I should just ditch thing thing and start a flickr account like everybody else. I mean, there are a lot of things that I use other servers for... I blog on livejournal, for example, even though I could easily start my own on sf (hell, I could run livejournal on sf, it's open source). I use my college e-mail more than my accounts on my server for important stuff.
I also know people who do tons of work on their own cars, but still go to wal-mart or whatever for oil changes. they just say that once you tally up the time, effort, disposal, and weigh it against the $30 it costs to just go pay someone to change it, you might as well just have someone else do it. The Man is more efficient than you. Most of us don't grow our own food anymore, even though it might be healthy to try once in a while (incidentally, I have changed my own oil before, just to learn what it's like) because the greater system is just easier. So it's hard to tell where those lines are, you know? And it's hard to tell where hosting online photos falls into all that... if it's like my forum, which I'd never give up in a million years, or my journal, which I just want to log into and not deal with any other details.