H-D's reliability has vastly improved since the Evo engine came out. I did 5000 miles one summer on an 11-year-old Suzuki Intruder, and swore by Suzukis. That was in '97, my last big ride. I bought an H-D XL 883 a few months ago, and love it. Taking it on a +3000 mile road trip in the fall. No...
As long as it's not a girly color, no. Actually, some guys prefer a women's specific frame, especially if they're not able to throw a leg over (older gents have that affliction).
I saved up and bought a Harley. That's what I did. You do whatever you want.
Sedona, here I come...
(The first time you do a 1000+ mile ride, you'll understand.)