I'm 30 years old and in the process of stretching right now. I have a couple of thoughts for you, because I am thinking things through especially as regards "grown-up" jewelry and possibly being able to wear the real stuff with actual cut stones and things ever again.
1. 10 is not very big. I was at a 10 last week, and when I took the posts out the hole looked pretty normal. Left them out overnight and it was hard to get the jewelry back in. Not a big deal, it would totally be OK to do that and still be able to wear post or wire earrings.
2. I think with this stretching trend that we're seeing, in a few years more jewelers, especially the more artistic craftspeople, will be making jewelry to fit stretched holes. There are already some beautiful pieces available in horn and bone, and with carved semi-precious stones. This is why I'm doing it, because I'm allergic to some metals and am hoping I can wear the organic materials. I can imagine beautiful designs with gold, silver, and stones. Maybe Titanium because it is lighter...
3. My mom and dh bought me a ring and pendant set for my birthday, like these.
We were in a jewelry store looking for a chain for the pendant, and I was browsing the jewelry. All of the earrings looked strange to me, and I could imagine how they would look as "piercing" jewelry instead, and to me it seemed like a much more fluid design choice. Looking at people with those wires and earring backs, I think they look weird, like there's this ugly extra metal bit attached to the earring so that it can go through that tiny hole.
I guess my point is that lots of kids are doing it (and grown-ups too) and yes, at the larger sizes it is more permanent. That means that it will be a lot more normal as these people get older, and jewelry will be made to suit and it won't be any big deal.
Just my 2 cents.