Most of the coaches should be able to give you good guidance. Things will become more clear in summer before senior year, when NESCAC coaches will ask admissions to do pre-reads on their list of recruits.
I recommend casting a wider net than just the NESCACs. Although there is a range of academics at NESCACs, they can all be intense. With that said, Trinity is probably the least academic of the subset of NESCACs that have football, but again, I would not call that an easy school by any means (many kids there have taken all honors/AP courses in HS, for example), nor do I know the extent of their LD supports.
Fit has to be the priority over football. I would be careful having an LD student use athletic recruiting to step it up in terms of school selectivity.