Heya Jay
Welcome to the club, and let me say you have excellent taste. I'm 41 and I hadn't ridden in about 15 years before I bought my TBA (has it REALLY been that long? Surely it was just yesterday!), however I did have a bit more experience than you, having previously been a motorcycle courier for many years. I'm also a short-a$$ levelling out at 5'8. My experience with getting on the America after a break was that it handles easilly and doesn't feel at all heavy or awkward. The pegs ARE fairly far forward and I found that stretching my legs out to them caused me a pain in the hips after a while but I got around that by having the dealer install footbards before I picked up the bike. With these I regularly ride hundreds of kilometers a day and use my bike EVERY day. In fact I recently returned from a 6 day, 2500km ride with a mate without any drama.
I've since used a friends TBA without the 'boards and it no longer causes me discomfort so I put it down to a lack of practice & unfamiliar exercise, but I'd still recommend the 'boards. I've owned my bike since Jan 04 when I purchased it new, and wouldn't swap it for any other bike currently on the market.