There are quite a few Hobie dealers in CT. Go
here and type in your zip code to find them.
I'm around your age, as long as you have no major physical limitations you need not worry about mounting the sail. The mast is carbon fiber so it is relatively lightweight. Once you've practiced a couple of times at home to get the technique down, you'll have no problems.
A bigger concern is having a trailer. The TI is too large and heavy to car-top. It's a breeze to launch with a trailer though, so be sure to include one.
The TI is an excellent boat for day sailing in relatively protected bodies of water. With some modifications, you can extend its use even more. It's very well-built and will last for well over a decade with proper care. I've used mine extensively since 2015 and it shows little signs of wear. It's a great kayak and a decent sailboat but don't expect it to perform as well as a dedicated sailboat. It's very easy and enjoyable to sail but it lacks performance sailing features some sailing enthusiasts might require.
It's great to see anything you're trying to buy up close and in person, but you can purchase a TI new online with full confidence. Hobie is an excellent company and stands behind its products. This is a top-of-the-line, dual-powered, day sailing kayak, there's little else out there to compete with it in its specific class. You can even motorize it for tri-power.
If you're buying used, and you can't easily travel to see it, then ask for detailed photos. If you post the photos on this forum, we'll give you our combined opinion as to what shape it's in and assess it for you.
I hope this helps. Feel free to ask any other questions you may have.