Well BigWil, that is a tough question, and I'm going to take the easy way out!
I love my VStar and I would not give it up for a Stryker!
That being said, you really need to assess your needs from a bike before deciding between the 2. My situation calls for the VStar. I don't ride it to work (have a company car) so it's not a commuter bike. I am married and my wife won't ride her own bike, so the 2-up comfort I get on the VStar is absolutley nessecary. We take several long trips, from 3 day weekend rides to week long get-a-ways. so traveling with luggage is vital to our rides. So the VStar works best for me in most areas. And it's a great bike to ride solo on some day cruises with my buddies.
Now I do like to dream, and one of my dreams is to own a second bike that would be MY bike, for the solo rides and just general runs around town. I'd want it to be a bad-ass ride. A bike with attitude! And the Stryker would fill that need. Or the Raider, but that's a different story...
The thing that drew me to the Stryker was the fact that it has the same drivetrain as my VStar. And I was curious about how that combo worked in that bike. (Grade A!)
Lastly, I think you either need to get to know your dealer better or find a different one. How do they sell bikes if you have to go through all that paperwork just for a test ride? My dealer has a simple form you fill out that has your name, address and DL #, and they make a copy of your DL. As long as you have a bike endorsement and proper riding gear, you can ride. I've been to a few other delaerships where I test drove bikes and most have a similar policy. The most detailed form I ever filled out was a Waiver form that took maybe 5 minutes to fill out.
Bottom line, you can't go wrong with either bike. That engine is bullet proof. I know guys with over 100,000 miles on it and have done nothing other than routine service on them. Good luck choosing, and enjoy whatever you buy!