Hi Mike,
You'll probably get more feedback if you post your questions in
General.
Just some thoughts:
Now that I have really looked at what is out there I like the look of the "naked" bikes. I have been looking at the Aprilia Shiver and the Monster line. I have really only sat on the Shiver and the new 696. I found the Shiver to be kind of uncomfortable, the angles of the seat and the tank didn't quit work for me. Right now I am seriously looking at the Monster line, but I am not sure if one of the bigger ones is right for me.
How was the fit of the 696 for you?
1 - My house is about 1.5 mile off of paved road and it is a lot of loose rock and sand.
Have you looked at the HyperMotard?
2 - I have been riding to work a lot more this year and it is about 35 miles (45 minutes) one way, mostly 4 lane highway 70mph, and I wear a backpack (have to haul my laptop around)
I also do the same, laptop in a backpack, but you might also think about a good tailbag. Have you looked at any sport touring bikes? Any BMWs?
The highway riding on my Sportster is not great, lots of vibration above 60ish. One question I have, is the more forward position better at higher speeds?
I think you will find the bikes you are looking at more comfortable on the highway than your HD, with less vibration. The more forward position should help with the wind as well as with cornering. Over long rides, being very far forward (as on some sportibkes) could be uncomfortable, but the Monster is more upright which makes it a nice all-around choice. You can also change the bars and rearsets to adjust the positioning.
Good luck in your search!