You can work it down to a fine answer, but I calculated our 270 Islander with twin F150s, with gear, accessories, fuel, water, batteries, ground tackle, etc as about 8000 lbs on the boat lift. I don’t see any way for you to be under 8100 with a trailer.
The Grady White web site gives the weight of the 275 w/o engines as 4972 lbs. The engines are 489, but you can call them 500 with oil in them. The performance tab shows 7866 lb. (including persons, fuel, water, gear, engines & accessories), so even if you subtract a bit for people you are over 7500 lobs without a trailer.
Bottom line, too much boat or not even truck.