I was in a very similar situation some 5 years ago.

I will add my 2 cents here.

Simply try and ride as many bikes as you can from the local shops. I would stick with the main guys as they have the most variation. Trek, Specialized, Giant and Cannondale. You would be surprised at the ride differences between manufacturers.

Case in point, I had my bike all picked out until a very nice rep from the Specialized store guided me into another model. For us larger and older guys, you will be better served with an endurance frame/fit. The bike is a tad more upright and that translates into more comfortable riding.

I bought a Specialized Secteur Elite Compact that was a year old and on sale. Got it for 950 which is slightly above your limit but it was a very nice bike. Compact gearing (50-34 in front) and a 9 speed. Shimano Tiagra groupset. Aluminum frame, stock Shimano wheelset.

I put almost 12k miles on that bike in 3 years without an issue. Tires of course, but no other issues with the exception of changing out my rear cassette from a max of 28 to a 30. I needed a bigger gear since I was riding a lot of hills, big hills at that. Blue Ridge Parkway stuff. Anyway, most of the bikes now come with 11-32 cassette so no problems there. I'd stay away from the triple in the front. More alignment issues and you really don't need it with 11-32 in the rear.

Like others have said, after a few years, you will get in better shape and want to upgrade. I did as my current bike was on sale for 30% off. Now riding a Felt Z3, full Ultegra and carbon frame. That was a huge jump in ride quality and shifting. So, you get what to pay for.

Key thing is, test ride a bunch of bikes. Keep your eyes open to sales. My current bike was 30 percent off because they were moving the shop to another location. That was 1000 off on the bike. I would never find a bike with a full Ultegra grupo and carbon for 2k. But it pays to look around.

Don't buy the first bike you ride though. Lastly, although Craigslist and used is definitely an option, as I said, every bike rides a bit differently and you can't really tell how you fit on the bike until you take it for a test spin. When I test rode my Felt, it was literally night and day from my Specialized.

You ride. Your fitness will get better and you might not be able to stay with the young guns but it will get better over time.

john