I dont think Tommy underestimates the MC in any aspect, not anymore at least.
He doesnt underestimate him anymore when it comes to the fighting, since the MC showed he could beat him.
And he doesnt underestimate the MC anymore when it comes to girls because of Quinn. And I say this because I think, according to a theory that I have, Quinn hasnt given herself to ANY guy in B&R (she only teases them). So the MC fucking Quinn (in public no less) is a huge feat in Tommys book
What I think is that Tommy OVERestimates Heathers love for him. Tommy doesnt care if the MC sees/shoots his shot to Heather because, in his own head, he has the firm belief that Heather would never let anyone close to her and that she is truly devoted to him.
And thats the reason why a Massive DIK like Tommy doesnt seem to be interested in Heather. He doesnt want a slime always sticking to him, he wants the forbidden fruits and women that have an edge to them (like the strippers and Quinn). He enjoys more the thrill of the conquering than the appreciation for what he already conquered.
What he doesnt know is that the MC is already starting to crack Heathers resistance
. And when her resistance is fully broken, Im really interested in what Tommys reaction is gonna be. Will it be a "well done
", or a "how could you?
"...