realskiers

Kikobb,
Welcome back to the world of skiing. Like you, I took over a decade off and returned to find that it's still the absolutely best way to spend time in winter. I've had many great experiences and meet many new friends, including several who post here. I was also overweight and undertrained and have since used skiing as motivation to correct those issues.

First, enjoy it. Just go skiing and suck in the experience. Your former skills don't disappear totally, at least on easier terrain. Don't push the envelope and make good decisions about the trails and speeds you go at. In your first few days, I'm not certain that equipment means that much. I skied on my old pencil skis and boots and got by just fine - I just didn't know any better. Getting good boots first makes a lot of sense as you can take them to Aspen/Stratton easily and rent skis. There are way more styles of skis these days and you may want to demo different types to figure out what you like. Airlines now charge $$ to carry skis, so some of the rental fees are offset. One issue remaining with new boots is that what feels good in the shop will probably end up being a too large boot as the liner compresses. Get your boots at a good ski shop and fitted by someone who is trained and does it full time.

I think you would be well served to take Stratton lessons prior to Aspen. You'll probably just work on basics like stance and balance, plus how to develop edging skills. Feedback from a good pair of trained eyes is needed. Many who post here are devoted to improving their skills and are students of specific schools of ski instruction led by Harald Harb or John Clendenin. Should you continue to ski, you will make a choice between learning to ride an edged ski or just push the tails to turn (pardon my gross simplification). You can have a lot of fun doing either.

Get some cardio work in for Aspen. Breathing in high elevations does not get easier as one ages, trust me.

Again, welcome back. Enjoy the ride!