If I were to ever get another Buell it would certainly be an XB. The maintenance is simple DIY. I think I still have a service manual and a seat that would fit yours.
Completely normal on an 03 Buell XB. Adjust the clutch per the manual. Check the adjustment 'shoe,' it's a wear part and could be ready for replacement. You can use HD trans fluid or motor oil in the trans. I always used 20w50 in both.
I'd like to see 1/4 mile times for the liquid cooled HD 750 vs. HD big twins. I'll bet the begginner bike nearly as "fast," probably "faster" with some basic mods.
Can you describe odd? After takeup mine breaks pretty cleanly in SA. DA is light, but a little gritty feeling. Not the best trigger I've felt, but good enough to shoot accruately.
There are tons of cool old bikes, I just need to remind myself not to buy them. I am only afraid of the old tech when I'm riding hundreds of miles from home in Buttplug, WV. Usually the louder the banjos, the better the riding.
Most of the used GW's I've seen have a shit ton of miles on them. So people must like them enough to actually be riding them. If I had to choose between a Hog and a Wing...I'd get an FJR.