the time sink that is synch

Am I just blind to the good solutions or does synchronizing data consume way more time and effort than it should?

I've given in and bought software that's supposed to be helpful for synching before, and it's never solved my problems. But I give up on smooth synching with mobile devices in general, and as long as I only buy apple hardware that side works well enough. What I really want is what should be the easy case: making specific data that's stored in desktop software available to others on the web.

How I imagine it: in iphoto I group some pictures in an album and assign them captions. I click a button to publish that album on a photo site of my choice. From then on when I click a sync button, any changes I've made locally are reflected on the web, and vice versa.

How it really is: I can batch upload some pictures to start. I lose the captions though there are for-pay maybe-solutions I haven't tried. From then on if I make a change in iphoto I have to log into the web site and make the same change. Even if I do something destructive like crop a photo and re-upload it, the web site will add the cropped version instead of updating the original.

This all puts inordinate pressure on me to get an album exactly the way I'll want it for all time before I publish it, which has the predictable result of making me avoid pictures entirely. In fact I don't even need web-to-iphoto sync, just iphoto-to-web. But it's like everything is written as if we're all submitting our final draft to the printing press.

I would be glad to abandon iphoto if something else accomplished this, but I honestly can't find any software that does this - not just for iphoto but any platform. Shouldn't be that hard? Aren't pictures one of the few things we all have in common? Even if I'm willing to deal with maintaining gallery or whatever open source software on my VPS (and I've worked hard to go the opposite direction) I still see no answers.

What am I missing?