I was looking at a Suzuki V Twin, in about 07?, and a salesman clued me in to a little something.
You gotta drop one of the pipes off the head just to change oil..

I went to check out the 950 today but I have to admit I was not as impressed as I thought I would be. Yes the bike has a bit more grunt than the S40 and I suspect it also has a higher top end, but it just was not what i expected. It was relatively comfortable though I felt I had to scoot up in the seat to reach everything properly. Also, having that hot exhaust right next to my leg was not fun (just like the Ducati scrambler). It seems that most every time a try another bike I appreciate the S40 even more. Having said that I still like the Yamaha MT07 and XSR700 a good bit. Oh well, I think maybe it is time to spend some mechanic-ing and money on the S40.

Springman:

I believe the Vulcan S would be a great fit for you......the only negative is the chain - but I think that is not a big deal with modern O-ring chains, as they are far easier to maintain than the old ones.  The lubricant is sealed inside, and the only cleaning and lubricating they need is to keep the dirt and rust off them.

The local bikes are in the $4,500 - $6,000 range for low mileage ones, and it won't be long before the prices get down to the range you are looking for.  The engine is reliable, durable and powerful...you won't have any problem cruising down the highway at 70+ mph.  There are different seat, handlebar and peg options for rider size.......that may affect which used bikes are right for you.  They are a cruiser that is not loaded down with a lot of extra weight.

If you can find one, try sitting on a Kawasaki W 650.

Come on over, you can sit on mine.
You can even ride the unicorn.

Duuude! Where's your sense of adventure?