ABVidale

On the final 98dd hand: (1) In your analysis you discount sets but I don't think you should.  Since 33 and 44 don't play well oop, and given your limp you will likely call, he may feel that disguising his hand by checking his option preflop is worthwhile.  If he misses, he can just fold (or decide to bluff); if he hits the unlikely set, you won't put him on that hand.

(2) Similarly, you discount the idea of him playing 2 pairs in this manner.  Since most of the time he would be slow-playing two pairs/sets, he may be using reverse psychology on you of donking, betting, and betting big on the river.  While it didn't work on this hand (you didn't call), you were confused so it is a reasonable strategy.

(3) I do like raising pre-flop with your hand.  You have a hand that plays well, you have position, and if you're 3-bet you can get a better idea of his hand and have a hand that's far better to play in position than Q6.

(4) As played, I agree that we don't know where we stand.  His hand feels like a bluff, but we don't beat much.  You were likely way ahead or way behind.  This is another reason for the preflop raise; we should be able to ascertain where we likely stand.

Definitely liked the video and the concepts presented.  On the third hand (~23 mins in), you note your opponent could have hands like KQ, flush draws, and bluffs such as small pairs & AJ.  I think another possibility would be medium pairs such as 88-TT, in which case he sees the raise as a value raise (whenever your c-bet is done with a missed flop)--not that it would change anything with the actual hand.