We're at about the same level, so here's my take on it:
Black 9: When you have a star stone in the far corner, I've usually seen the solid connection version of the joseki used instead. I don't know if that's a strong principle or just personal taste, though.
Black 37: As a general principle, when presented with a case where you need to connect, and you have a choice between the solid, obvious move and a cute move, where the cute move prevents being cut immediately but not forever, choose the solid move. If you read deeply and liked the outcome you got in the game when you made played black 37, then I guess it's fine. But otherwise I'd say you were lucky to have it work out as well as it did. And considering the weak black group in the center caused issues down the road, I don't think being cut in two is a good result for you
Even with a huge corner.Black 61/64: Yep, this feels wrong. Not sure what the right answer is. Maybe set up the ladder, let white cut, and then use it to make two moves in a row (ladder breaker + followup) on the far corner. You should be able to enclose the C14 white group with two moves. Or actually, maybe just make the ladder breaker + followup without setting up the ladder. If you're lucky and white decides the local threat outweighs the ladder and responds, you then set up the ladder, and basically got a move on the far side for free out of the exchange plus a working ladder. And it's at least sort of subtle and tricky so you might get white responding just out of habit.
Black 69: Hmm, maybe there's a tesuji here? Something like N11 almost seems to work, but white M13 puts you with a shortage of liberties. I guess this says that N12 should have been an urgent move for you. Probably instead of black 51. You let white rip you to shreds on the bottom, but can't be helped.
Black 119: Moves like this never seem to work in my games either :/
Black 191: Finish what you started or you make 189 seem a bit silly. N4. You can always save the stones by capturing at K8. Unless there's some tricky line of play I don't see.
can be in either position. I looked up the entire side position in eidogo's pro game database and found examples of both plays in positions just like this. There were also a ton of examples of pros not playing the extension on move 11, or playing a dual extension / corner enclosure oogeima at C13, etc. I think there are many fine ways to play here.