Welcome Matt, and thank you for your service!
Now on to the bikes. Hate it but it is true, I would go with a speedy being as how triumph corp has the slash cuts on the speedy now. That and the bars being narrower. However, imho anything after '08 looks like the nether regions of Roseanne Barr's rear end.

Highly advocate anything prior to the buttazz fugly tanks, mag wheels amoung other pointless rantisical items.
The benefits of having a motorsickle that you can remove the cam cover of without removing the tank, the fact that your fist can slide in next to the head tube and well never mind. Dangit man.. Recalls to mind some words penned by Randy Newman,
"Sister Sue is short and stout,
She didn't grow up, she grew out.
Momma says she's plain, but she's just being kind.
Papa thinks she's pretty, but he's almost blind.
Don't let her out much except at night.
But I don't care 'cause I'm all right."
sorta like a sweet and sour candy, being able to map the fuel systems would be sweet as would being able to plug a flat.
Used americas and speedies have all the classic components and looks. might consider breathing new life into someone's used, 270 crank motorsickle.