Well my fixes seem to be holding up. I drove 150 miles today on paved mountain roads. Some cruising, some spirited driving, some slower windy roads. Definitely not extended time at 5500rpm or even 5000rpm, but often going through the usable powerband briefly between turns (3k-5.5k rpm).
It was extremely liberating after all the work I've put into the bike. While riding my temperature gauge only goes up about 1/3rd and I never heard the fan kick on once. The fan is working, if I let the bike idle long enough it warms up to halfway until I'm moving again. I ordered a replacement 195F t-stat for my T-Bob version 1, hopefully that's the fix.
I haven't removed the factory t-stat housing since owning the bike, but my understanding is that they open early (cold) anyway. I might test my old t-stat once I drain the coolant. I'm hoping if it indeed runs warmer after a new t-stat that the oil viscosity difference, however small it might be, helps the engine smooth out a bit. The engine isn't very happy between 2-3k rpm, but seems great everywhere else.
Perhaps a carb cleaning will help with this too. At lower rpms I get intermittent exhaust pops during deceleration, I'm thinking something's either a tad dirty or in need of slight adjustment for more fuel in partial throttle (low throttle) positions. Not going to lie, I plan on riding more before getting into the next project with the bike...as long as nothing breaks haha