Joined: Apr 2011
Posts: 4,073
Likes: 16
From: Minnesota/Arizona and between
Bikes: Bike Friday All-Day (ebike), Terry Classic, Serotta FIerte, Trek Cali carbon hardtail, 1969 Schwinn Collegiate, Kona Explosif hardtail, Catrike VIllager
If you go for a road bike make sure it will take at least 28 width tires. My Trek Madone will not.
Jamis Endura is a nice road bike that will take the wider tires.
I think I would be hesitant to buy a hybrid or flat bar road bike in the $2000 range unless you are prepared to spend more money later on a different style bike. The issue is that the bikes are compromise bikes. If you find that you like really long rides or if you have hand issues a road bike or cross bike with their multiple hand positions may make more sense. If you go the hybrid route to see if you like biking I would consider a cheaper one and then buy another bike later when you know better what you want. I have a road bike and assorted hybrids or hybridized bikes. I find that I ride them all, but in different situations. For example, the hybrids are especially nice for riding around towns with their upright position.
You also might think about a Salsa Vaya or Surly Cross check. They will take tires much wider even than the 28s and even though they are steel they really aren't tanks.