Not sure if this was already mentioned earlier or not but Don't forget to check the removable plug boots. Many have replaced TDI's and coils only to find the plug boots were faulty. If you look close you can see that the internal parts of the OEM plug boots can be removed, inspected and cleaned on the 1st and 2nd gens. They can get corroded inside which cause them to fail.
One would think that after owning this bike for 27 years, I would instinctively know the most basic of the safety features - but give Larrydr a cupie doll - the kickstand WAS down and that was why it was shutting down when I was putting it in gear in the garage on the big stand (duh). The transmission seems fine now that I can put it in gear. But the brake is definitely hanging up - so the first and simplest diagnosis was the correct one - stuck brake. So now I just need to pull it apart and determine why. I replaced everything but the piston on the brake about 4 years ago but have not put a lot of miles on it since then (and all local travel) - and it has only been out twice this year until I got the speedo lubed up. The comment about the washer on the wrong spot on the rear axle makes me curious, though I thought I was pretty careful to put everything back the way I found it when i had the wheel off. Thanks for all the thought you folks put into this and the suggestions. Certainly a big relief that the transmission is not the culprit.
So, I made contact with Mark at Diamond Seats in FL... Mark was pretty confident that he could get me two inches higher and four inches back, which I figure is about what I need... he is going to contour it better for my fat azz too... 6-8 weeks delivery sucks but I am happy to have a light at the end of the tunnel on my seat comfort issues... a poor seat is a shitty reason to sell a nice bike. I will report back to this thread once I have tried the seat out.
Figured I should update this. I ran seafoam through the system, replaced spark plugs, cleaned air filters, oil and filter change, adjusted the idle (it was too low) and did a carb sync. Tremendous improvement to how she is running/performing.
I changed my driver's back rest out.
I went from a Chinese eBay special to an American made eBay special. The Chinese rest was adjustable but could not be easily removed, and I could never dial in the adjustment. The Grasshopper, LTD back rest is not adjustable but it comes on and off easily and quickly. The default position works pretty darn well for me too.