Looking good so far, John. Not to second guess the Titan guys, but you may want to consider starting with larger mains. Not sure what the fuel is like in SF, but I have alcohol here. I presume you have made no modifications aside from the pipes and air cleaners and while the T500 motors were designed as more of a bomb proof touring application than a hot rod, better safe than sorry. I didn't glean how much 2t tuning experience you have from your thread, but they are a sensitive disaster compared to 4 cycle engines, some more than others. You risk possible serious problems working your way up to rich enough instead of working your way down to lean enough, especially if you are not certain what safe spark timing is and you run the engine hard. If you are using alcohol corrupted gasoline, start with less than stock advance too. Like the jetting, you can always work your way back once you know you are safe. There can be a surprising variance depending on setup. I have a 350 in my shop now that likes 280 mains up from 140 stock. More engine mods than your bike, but that is a big increase - I thought it had to be sucking air from somewhere but is tight and runs fabulous like it is ready to grenade. Plug chops are textbook and it is at 1800 miles. I have another with 34's on it, my personal bike, highly modified and it likes only 270 mains so go figure. Everything I see runs too hot with stock ignition timing running the pump gas with alcohol. Straight gasoline without alcohol is hard to find where I live, so I just have to put up with the alcohol.
I have gone to using Rotella in my 2t transmissions and while it seems like it would be a heavy horsepower robbing fluid, it doesn't seem to run that way and I am seeing better shifting and no clutch issues. I am using the non synthetic. I use Yamaha or Bel-Ray fork oil, though I have never seen any brand that I thought made any difference. Experimenting with volume and viscosity makes giant differences, but have never seen one brand to be better (or worse) than another. I have never used anything other than dedicated fork oil, so no opinion on using atf or anything as a substitute.
Practically anything will be a giant improvement over the stock shocks. Mostly, shocks are a "you get what you pay for" situation, and I generally make suspension the main focus of where money goes into a project. The T500 has a long and frail frame, so the is no doubt a point of diminishing returns seen pretty rapidly without frame mods, but don't overlook the all important swing arm pivot when getting all you can out of the stock chassis.