I'm sure there's an excellent strategy for everything, but sometimes it's better to get it done than waiting to get it done exactly right. I usually end up making a ton of new things at once, and photographing them all at the same time. My plan is always to have several listed at the same time and then roll out, but as usual, the plan don't always work out...
I say, get as much out of the way as you can and see what happens. If you have different tags for them, then you'll have a few in different searches, which is probably what you want anyway.
Best of luck with #2- sure changes the game!