Trub loss in the fermentor? Plan on 2.5 gal into the fermentor and, on your next batch, measure the trub level in the fermentor (if marked for volume) or the beer bottled out of the fermentor.
Trub loss in the process, plan on a post boil volume of 2.75 gal and see how much is actually left over when you put 2.5 gal into the fermentor. You can then look and see if there was more you could have put into the fermentor or if you ran a little short and then adjust your 0.25 gal overage accordingly. Enter this as your loss to trub and adjust your planned brew back to 2.5 gal.
In my system, I plan on brewing 11 liters post-boil, with 10 liters going to the fermentor and 1 liter as trub. In most of the recipes I make, I could take the trub down to about 0.5 liters, but I like the consistency of filling my fermentor to the 10 liter mark and measuring what is left. In high hop loaded IPAs and DIPAs, I end up with right around 1 liter of trub.