Thanks for your insights. Not sure that I "loved" the Schwinn - it was the only road bike I have ever ridden and finances were tight growing up, so I didn't have a choice of bikes. I don't even recall if it fit me (come to think of it, I never adjusted the seat, had tune ups or even knew to oil the chain!). I don't remember what it felt like to ride it, but I do recall I learned to ride with no hands and could go literally miles with no hands if I wanted.
Heck, I don't even have a budget in mind. Probably not more than around $1,000. We have a place called Sellwood Cycle Repair that sells new (Kona dealer) and excellent quality used bikes on consignment. So a used bike would be an option. I looked at the Trek Portland Which Trek calls both a "Road" and an "Urban" and my favorite LBS happens to deal in Trek. It's more than $1,000, so...I guess if I totally fell in love I would consider something more.
I don't think I want carbon because I don't see myself ever needing that "much" specialty in a bike for my type of riding. Steel sounds heavy and I doubt I'd ever be riding more than perhaps 30 miles in a day (although who knows?).
It rains here a lot, so disc brakes sound nice. I don't work so commuting to/from work isn't an issue, although who's to say?
I think I might like an all around general purpose road bike to ride mostly in urban settings vs century type rides.
Portland is opening up it's first ever indoor MTB park similar to Ray's MTB in Cleveland. I've never ridden a contain bike, but want to try. We have some MTB specific shops in town and I think they have clinics. so I would definitely try different types od riding before buying a new one.