As the subject says, I just got my first TTSE. Having "upgraded" from a Honda ST1100, so am no stranger to pulling off fairings to do maintenance.
As a word of encouragement to anyone wanting to do their own basic service - there is nothing "difficult" about any of it. If anything, the Trophy is beautifully designed with all the same bolts for every hole. If you find a longer or shorter one, or something with a different head, odds are you've gone off course.
The flip out mirrors are frustratingly brilliant. It did take an embarrassingly long time to figure out how to get to those bolts.

Draining the fuel tank is obvious once you reach that point, and unfortunately, there does not seem to be any way around this step, so as people have mentioned, the less you have in the tank to begin, the better. Of course mine was 80% full, so a little stool to put the jerry can on was an absolute must.
The air filter box is a similarly brilliant design, though I am very glad I was in a good mood that day. Why they used torx screws is a bit of a mystery. I may swap those out in a future visit. I can't imagine paying a shop $150/hour to do what should be one of the most basic maintenance tasks in owning any vehicle.
All told, including replacing a worn radiator hose on the left side of the bike, the air filter and an oil change, it was a 5 hour project with nothing but basic hand tools. Next time will be quicker and less stressful for sure. Filters were comparable in price to my Honda, and the rad hose direct from Triumph was only $25. That was a pleasant surprise. I added a few goodies like wobble hex-wrenches and a better screwdriver to the tool bag on the bike. There is nothing like doing your own maintenance to build confidence in the bike you ride, especially for long distance adventurers.
Hope this helps anyone afraid of what looks like a very complex setup some confidence to give it a shot.
Cheers,
/Kris