Welcome Bill from another M3W newbie!
1.- Endemic Issues/Reliability - I have put 2,800 miles on the beast since delivery and have had only the one glitch with the rectifier/regulator which is a known item. Easily repaired by, oh, anyone and that would be me. Most any Harley mechanic will have this one nailed and have the replacement parts available. Bump Steer - ah, a known goodie. Where you are, this may not even be an issue unless you hit roadkill. Please try to avoid. It is no fun. Where I am in New England, with ground freeze during the winter, spring thaw and the occasional hurricane, the roads are pretty much crap in Vermont. Good roads are a joy in the Morgan. Bad roads make one wish one were elsewhere...
Bevel box is a big unknown. The whine has dropped appreciably and time and miles have helped but the rest is due to the driver learning just how the engine/transmission interface works on this car and what the drivetrain likes. It gets noisy when it doesn't like it. See the bits about sealing the cockpit from the rear and all the tricks about the so-called trunk. All of it helps.
2.- Superdry. If you want to be aligned with a Japanese clothing retailer then have at it, or get the basic and modify to your hearts desire. I held off on the chrome package and you may have a think about that. The chrome headlamp buckets get very bright in the sun where you are and are a big distraction. I bought the basic Blue with tan leather. People love it. My only statement was the Union Jack on the side. The women think it's cute. Who am I to argue?
3.- Dealer. Whoever is close and convenient works. How are they for doing the weird stuff like modifying body work or adding a luggage rack? Something I am seriously considering as this thing has the carrying capacity of a Kleenex box... Harley-Davidson mechanics will be working on the S&S, hopefully. Parts are mostly interchangeable. I don't expect much grief from the Mazda gear box.
4.- Texas. You're on your own. YOYO
I agree. This is a great forum! It has saved my sorry a@# already!