I lost 110 lbs over 18 months from age 27-29. I had been been obese since adolescence. I had a lot of loose skin - it was the worst on my stomach and the skin fold would cause problems when I was active.
I was still a million times happier being an average size with the loose skin than I was when I was fat. For the most part, people couldn't even tell I had loose skin because I would tuck it in to all of my pants.
In the end I got the tummy tuck and am now a trillion times happier than when I was fat. I was lucky and my insurance paid for about two-thirds of the cost (and I picked an expensive surgeon - if I had gone somewhere cheaper I could probably avoided paying out of pocket.) I know this wouldn't be a choice for everyone, but know that once you get to goal, you can wait and see if you have a skin problem, and if so, there are options.
Now I'm just left with the extra skin on my breasts, arms, and thighs, but I'm not seriously considering any more surgery. I'll never be perfect, but I'm perfectly happy being healthy