Here's one tip about pitch - wish I had a pic to show this...can't get a decent image with my crappy camera.
The bigger pitch chains have the advantage of having a lot more material that can be removed before the chain can't be sharpened any more. So, a .404 chain has 29 mils (.75mm) more top plate length (probably 2-5 sharpenings) than a .375 chain. The .325 links look positively anemic compared to the .404 - from a glance it seems like they'll only get about 1/2 as many sharpenings. Seems like this would be more significant if one was working 30degree cutters down for milling.
OTOH, since chains stretch and wear with use, it may not be good to use the same chain over and over. Stretched chains tend to wear sprockets and while rims are cheap, I don't know too many folks that change rims along with chains to ensure even wear. I've never worked a chain all the way down to the nub before I decided that it was too floppy to keep using. (am a bit afraid of a broken chain, dono why)
Somewhere in there is a compromise that works for a lot of people.