When I started riding again about 18 months ago, I began on a hybrid. Within a month I bought a road bike. I don't think I'd have stuck with it if I hadn't. I didn't really start to enjoy it until I got on a road bike. Maybe it was ancient muscle memory from riding a road bike as a kid, but I found it orders of magnitude more comfortable than a hybrid. I'm sure it's a very individual thing, but I wouldn't approach the transition with the idea that a road bike is going to be less comfortable. Some folks may find that to be true, but for me it was exactly the opposite. And I doubt I'm the only person on the road who feels that way.