From my POV I would suggest you ride on smooth pavement, pick some routes going out from home in every direction, that way you can choose to ride INTO the wind on the way out, and with it at your back on the way back, or if your a glutton for punishment do it the other way :-). You can also tailor it hilly on the way out and flat on the way back, etc.
I have come closer to crashing into other people doing silly things on multi use trails than on good old surface streets.
I may have just gotten lucky so far but this bike has served me well so far for 220 miles in June :-).
I am SO glad when we bought those bikes we got that year because after that they had suspension forks.......suspension might be fine for some situations but I never ride off pavement.....and it would be contrary to what I am doing right now.
Those wheels seem fine so far, but I WILL get off and walk if I have to if the situation demands it (had to yesterday....they were spraying liquid tar into some road cracks, had to walk the bike and lift over the good for about 1/10 of a mile).
2001 Trek 7200 - BikePedia
I started this month at 279.6 so I was in your weight range then.
I like the 3x8 setup even though I almost always ride the middle chain ring, a so called "compact" 2x8 setup would probably actually serve you better overall, less shifting, you would probably start on the small ring up front and graduate onto the bigger one with more miles. I'm thinking of going to a compact setup up front.
That trek is setup for fenders too which might be good if you want to be able to ride in the rain, or right after it rains.
So that is my .02....I did not need any special wheels to handle my weight so far, we will see :-).
Bill