I tried to address all your comments so there is quite a lot of unorganized material.

should be a bad invasion point, but white got a good result in the game.

looks like bad shape. If you play the same sequence by omitting it it should be better.
After

white is living but black should except outside influence. However connecting at

is bad shape because of

. Imagine the situation without

: white must live on the right and you get to capture the cutting stone.

looks bad. F2 is strictly better in terms of points. Tenuki looks unreasonable, E2 would give you trouble to live. After

the result is good for white.

is unusual but it might be a situation where it is very good. But in the fight you are right that

should cut the other side.

is overplay. White should cut at H15 then extend at J15 and you cannot capture the stone. You should connect at H15 instead and be satisfied. Obviously the result in the game is excellent for you.

I prefer your move, P18 would give white O18 to make miai of an eye on the right or the left.

I like your move. Q5 also looks possible. Anyway you have ladder problems, so taking the stone in the ladder is an option.

as you saw should go out of the ladder.

tactical amelioration: you should atari at D15 first. This solves all your problems at D14. Then you can play a loose ladder as in the game if you prefer.

your shape is in tatters. I'm not sure there is a good shape move, maybe E12? Tenuki is an option to attack bottom right. As you saw

is a big overplay.

looks a early, but it's hard to read. White's answer should have put you in trouble. In my opinion you should play O10 to make points and prepare the attack on the top.

yes, white should have taken the stones and the group would be unkillable.
b101: it happens. There was no way for you to save your stones even before, so T13 was a mistake. If you played 101 instead of 99, it would have been a nice attack on the bottom stones.
b109 also looks like bad shape. I think simply Q15 gives you a better result.
b119 is a nice idea, but it shouldn't work so well (120 is very submissive).
b133 is also a nice idea but unfortunately it doesn't work. At move 134 white can play F11 G10 F12 connect G12 connect H10. After this mistake I don't think white can do anything. Your suggestion at 140 looks correct but it is still a good result for black.
For your suggestion at 148 black can play K11. At move 153 in the variation black plays J11 and everything works.