Update,
As of yesterday, I have been to seven shops. One was closed and moved to Florida, with a still functioning website. Three don't even carry the bikes they have listed on their websites.
One was iffy and two were very good.
No bike yet and more questions than answers. To date I have test rode flat bar road bikes, dual sports, 29ers and a cyclocross bike.
I tried a Raleigh Talus 29, and a few of their hybrid bikes, a Cannondale CX4, an older but new KHS CX-200, a Trek Stache 7 and a few others.
Out of all of them I think I liked the cyclocross bike the best. The Stache 7 was sweet, but I'm not sure I want to go that far to the dirt side or spend that much.
Nobody seems to have Surly bikes within two hours of me. The Jamis line is the same way. A lot of websites list them, but no bikes on the ground. Not surprising, I live in the sticks. Lesson learned = call ahead to verify prior to driving and hour.
Trying to find a bike that ticks all the boxes while still coming in around budget is proving to be a juggling act with some give and take. Like on a cyclocross bike. I like the fit, but many don't have braze-ons for racks. I see there are work arounds for that. But also some of the gearing might not work for me.
What I have learned is, a full blown didicated road bike is probably out for me. I may try a bike like the Trek 7.4 FX just to see how it feels.
But I am liking the thought of the C-Cross bikes with their turn down bars, beefier tires, and more relaxed frame geometry, and multiple hand position options. On the flats, I am up high, on the hoods I am in the middle, and on the drops, I am as aerodynamic as a 250 pound fat guy can be on a bicycle. The one I rode also had interupter brakes. This may be blasphemy, but I liked them.
I was sure I would own a bike by now. But the research has proven valuable. My original target bikes have moved further down the line in favor of ones I didn't think I would even consider.
One thing I have noticed is if I go the Cyclocross route, I will most likely have to increase my budget.
One other thing I noticed. I am in piss poor shape. Back to back bike trials of bikes in hilly terrain have alerted my legs of things to come. I guess it is a good sign that my legs fail before my lungs and heart though.
Thanks again to everyone for the comments and advice so far, I will keep you informed as things progress
Dack,