Craig - If you look in my sig you'll see all the experiments that are currently bottled. Doing a quick bottle count, it looks like 24 bottled to drink, not including the 3 big bottles (1L) of cider for the SWMBO or the 28 bottles that are conditioning (AZB will be done this weekend and ready to serve, OOA will be ready in two weeks). I usually try to keep 36 bottles of varying beers in the crate downstairs, then put six into a old sixpack carton and put it in the main fridge up stairs. When the carton gets low, I grab a new mix of beers.
On the pipeline side, I usually have 3 carboys running (this is an odd week, so only two running right now) and have bottling day on Sat to collect the yeast slurry, then brew on Sun and repitch that slurry into the new beer. Because of that, I try to time it out so a beer that uses US05 will be made after I bottle a beer made with US05. That allows me to not really worry about conditioning time in the carboy, and get a few uses out of my yeast.
Bottles I'm standardized on Sierra Nevada/Alaskan/Summit style bottles (shorties). I like the looks of them, no real reason. I did run into issues trying to put them into a milkcrate for storage, they don't fit well. If I was starting out, I'd choose a standard sized bottle (tall/skinny) with a good lip on it (like Sam Adams) for the bottler. Oh who am I kidding, I should have skipped the wing capper and gotten a bench capper right from the start. It's on my purchase list as soon as I find one of those oldschool metal bench cappers.
I'm not sure what the lifespan of a bottle is - like anything I figure there's got to be a limit to the number of times you can cap a glass bottle before it starts to develop issues. When that happens I'll like migrate over to the tall bottles. To get them I just bought a 12pack of SN or Alaskan while my pipeline was filling. Alaskan's were MUCH EASIER to delable and clean. If you go this route, pick a bottle that's got only one label on it, instead of a top/bottom/back labels. Less to clean off after an Oxyclean soak.
I've never used the Grolsch style bottles, so I'm of no help - I usually just buy the cheap gold caps (like 3 bucks for 144 caps) and have not had a problem one.
Eventually I want to get a couple cases of 16oz bottles (likely from Hinterland), so I can do bigger ABV beers in them for one and done nights. I'm not a fan of bombers - heresy I know, but I don't drink them fast enough to keep them nice and cold, and I don't like leaving an open bottle in the fridge.