Heya lauren! Ditto on the claw clips. I used them almost exclusively before my transition, mostly out of that very fear of pulling ponies too tightly, and they give you a bunch of ways to hold your hair up and out of the way without any risk of damage. Before I go to sleep, I often just pull the whole thing into a slightly loose knot, that sometimes works its way open during the night, but not always.
My wife occasionally braids mine for me, and I've worn it for days at a time, with no discomfort. It just starts to look a little ragged after a day or so.
I had a round of transplants at the end of last year, and may do one more round this fall, but my hair is way too curly to make bangs a practical option, so I'm just wearing someone else's bangs for a few more months!

I find that wig shops are really good places to see how different styles actually look on you. There are a few styles that I finally had to give up on, because they just didn't look as cute on me as I imagined they would. But I was also surprised at how good some others did look, ones that I might never have picked out for myself.
Good luck, and hope you have some fun developing your style!
Erin