Here is my experience for what it's worth. I'm 56, diabetic and about 250 lbs. Like you, I rode as a teen but stopped. About 18 months ago I bought a Gary Fisher hybrid and really got into riding. I joined a club and really enjoyed myself. Quite frankly, I found that I couldn't keep up with many rides, couldn't get up hills comfortably and couldn't maintain much speed. Still, being on the bike was wonderful.
A month ago I bought a new 2006 leftover road bike (Felt F80) and I couldn't be happier. I immediately lost 15 lbs of bike weight and it makes an amazing difference. Pounds of body weight are dropping too. The more I ride, the more I lose and the more I lose the more I want to ride. While no one will ever mistake me for Lance and I am resigned to never have a Whippet like road body, I'm really feeling better about myself.
I was worried about the leaning position and had brakes installed (only $25.00) on the top bar but after the first 50 miles I find myself on the hoods 90% of the time. It's nice to have the extra brakes but aclimating to the road position came quickly and naturally.
Since this is a major purchase, look ahead regarding the type of riding you'd like to do a year or two from now.
Best of luck!!!