1) Are you a big guy?

2) If you have the bars at about the same level as the saddle, that really helps with the comfort.
As does the long wheelbase, and larger/lower pressure tires.

3) don't worry about the parts, except the saddle.

4) the two bikes are completely different. The Windsor is a racy bike, and it prob has a fairly stiff ride. The LHT is a touring bike, with a pretty nice ride.
In between the two is the Sport category. The Surly Pacer is a good example.

5) At a grand, the Surly Cross Check Complete would be something to look at. In general, I'd look for steel frames and relaxed geometry. You should hit a few bike shops and test ride some bikes. See what you actually like when you're riding it.