I like tattoos when there's some sort of a symbol or text.. and when they aren't covering entire part of the body.
Just like any other kind of art it's the quality - how good it looks what matters the most.
Many tattoos are bad and they suck. But many tattoos look really great!
About wings on your back.. it sounds really weird and stupid but when I see such thing it makes me wonder why don't you have 'real' wings but just a big image of them on your back? It's kinda dizzying to me.. not really good vibe. A rose or a star would look so much better!
I'd much rather have a girl talk to me about the fun things she's done in life -- sky diving, or vacation trips, or scuba, or whatever -- than to find out she gives herself 'merit badges' on her skin for them.
It all depends if you can pull it off, really. But if you're going to get something that big, that permanent and that potentially painful then be sure it's what you really want. Wings are BEYOND cliche and getting them as a memento for having gone skydiving seems like a really weak excuse. Oh, also that tattoo, if done well, will cost A LOT. Wings aren't as simple as a peace sign and any place worth going for that kind of thing generally charges 60 dollars minimum, for something small/average sized and easy. This is none of those so expect to pay well over 100 bucks.
To me it just doesn't seem worth it, it seems tacky and cliche. If you really want to get a back tattoo get something that's actually going to be powerful and connect with you. Especially the reasoning seems weak and boring. Yes yes, wings because you're flying. Except you can't fly, you're falling.
It seems very tacky to me. But I'm not a boy so my opinion might not weigh as heavily.