So I'm happy with my camera and cataloging software, Nikon D70 and iView MediaPro. Step 3 is uploading software, step 4 is photo hosting site, step 5 is blogging site. Clearly it would be best if 3-4-5 were all the same place, and worked with iView. Seems I can't get that to happen. My first option for photo hosting was LiveJournal's ScrapBook service, since I already pay for LJ. Nope, their upload software is bleh, for Mac users not using iPhoto anyway. Second would be Gallery2, which I have installed on my webserver, but I'm not really currently using. The biggest problem with that was Gallery's poor support of IPTC. I don't want to have to rename my photos just so that it gets the title right, I ought to be able to get it to pull the Title from the IPTC data, which I've already annotated in iView. So, third choice, Flickr, potentially yet another service for me to pay for to get decent service. Oh well, so far it's working the best.
Current workflow, which seems to work relatively painlessly, is: catalog in iView, internally to iView I can select a set of pictures, and control click to open them with PictureSync. PictureSync makes a pretty good bridge between iView and Flickr. (Really it makes a pretty good bridge between a lot of services.) It correctly grabs my titles and other IPTC tags, and even sends the pictures back to iView to be rotated and resized for the web before uploading. Woo! I don't have to save any intermediate files, everything is taken care of very cleanly. Color conversions even happen inside iView, which I can get to do things 'right', theoretically. Excellent. So now the pictures are correctly tagged, and hosted on Flickr. Turns out Flickr has a 'blog this photo' link on every photo page, which happens to play well with LiveJournal. Since it isn't really blog specific it isn't going to let me set all of the custom LJ-y things like icon, mood, whatever, but it does nicely take my text and stick a pretty thumbnail image in the corner of my post. And if I really care, it puts up a link to take you to the entry after you submit it, where I can edit the thing and set LJ stuff if I feel like it. So it seems like Flickr is really a pretty good solution, technology wise.
Social wise, it might mean setting up Flickr and LJ accounts for all of the relevant relatives if I want to protect things. Not the most convenient thing then, to have the blog and pictures on different sites. But LJ is good at blogging, and Flickr is good at photos. Meh.