Well, im glad you brough piosolver up. The main problem with overbetting is that in some spots the players are simply not balanced enough (not bluffing the river enough). So when looking at piosolver, im sure it suggests interesting hands to be used as bluff. And if you are willing to balance that in the right way, then yes, I suggest overbetting. However, I think that the majority of nl500z field (so excluding top regs) would not get the idea to overbet the river here with air in my experience.
There is also a matter of history between the two of us :), he knows that I do not mind calling big bets on the river, and hes aware I would never fold the top of my range in this spot. So I think he was just trying to exploit me by overbetting.

Hi holabcn!
30:40 this hand was a huge mess unfortunately :) 7s are just the bottom of my range so I decided to try and scare him off. In other words, I was hoping he has a weak part of his range, so AQ, KK or AA (no club in either case), not sure if hes capable of squeezing KQ or KJ or AJ, but his overall 3bet was 10 (not a big sample though). It was a little too optimistic on my side and I was aware that hes not folding too much of his range but i just wanted to give it a go. I guess if I had 7s without a club it would be an even weaker hand, with a club checking back and giving up, hoping to get a 4th club is not a bad idea.
36:40: This was vs a player I 3bet quite a lot in this session, I had a feeling he was getting annoyed, and on this flop I think he would assume I'm overbluffing and he would probably float too many hands. On the turn, I cannot x-f this hand, i must x-c, and since I will have Ts, Js Qs, and better 9x hands to x-c, this one just felt to weak for me to bluff catch with. So its more of a preference thing, I am more comfortable here to maintain the aggressive approach rather than pass on this opportunity to him. Additionally, I had a clear plan what to do if I get called, there are no rivers which will make life difficult for me. And if it happens that he folds the turn, I am very happy :)
41:40: The problem is, when player 1 calls the turn, he is either calling with a set, or a potential AK combos, I really doubt he would ever call flop with AQss so I can assume that is out of his range. I'm guessing if there is going to be a hand that he will fold on the river it will probably be only 4s(assuming he doesn't raise them on the flop). So I'm really not happy with fold equity on the river, and I think I would probably give up.

Hi Ben,
19:15 - on the turn I can get him to fold low pocket pairs with this bet size, I also thought he would call the flop a lot so I can get him to fold K-9/8/7..They are of same strength as my hand but I do not want to split the pot. Also whenever I x, I am completely face up, which makes me vulnerable on the river to a bet.
35:41 - Pocket Ts were a squeeze, and 97 was a normal 3bet, so my pf ranges are different there. Sqeezing range is a lot tighter(therefore stronger) than my usual 3bet range. Also, when I squeeze and he calls, I have a lot more info about his hand, and I know his range is not too wide, so 30-35% bet does the job whether it is a value or protection or bluff bet. On the other hand, with 97, I think betting 60-65% is on the flop is also fine.
40:10 - I will have AK combos to bluff, I wont bluff all of them however, I have to be careful. Also hands like 6-5, 7-6. Even though im IP his 4bet was quite large so I cannot call too much pf, so I will be stuck with a lot of AK combos.
41:15 - It is not a great hand vs people's calling range but a small bet gives me a chance to see the river (if turn goes x-x) and potentially improvise later on, and also betting may get at least one of them to fold, so its a lot easier to play vs 1 than vs 2 players later on.
46:18 - yes, 4-5 does bet AQ AK, but that isnt all that he has in his range. This player is really good and on this flop, vs my MP3bet calling range he can afford to x many overpairs. So just because he checked flop, does not mean that he never has QQ KK even AA. So if he cbet the flop, I would call 4-5, cant fold especially with a diamond on the board. However, once turn is a 6, 54 really becomes the bottom of my range. Also, since I know that he will x this flop with overpairs, I can play a mixed strategy with sets, 2pair and straight combos, meaning that I will not always come out firing on the turn, but I would rather x and then raise. So as I was playing, I thought about x-r 5-4 and shoving river, but I could think of better combos to do it with so I just folded 5-4.

Hi depstack,
Yes, I am getting 3 streets of value from his overpairs if i just x-c, but that only happens if turn and river are blank cards. For example, if turn or river card is an ace, then I lose my value completely. The second reason I raised is because the board is really draw heavy. I 3bet on sb vs button, thats probably a position I 3bet the most, and since I will only fold about 50% vs 4bet, I will have quite a lot of combos to play with on the flop. So hands like AJdd I would x-r, JTdd, even ATdd(but I wont always call a 4bet with this) just to name a few. Either way, as long as its a board with a lot of draws he can never fold, in fact you do not need to have any bluff raises and you will still end up allin vs KK AA.
So yes, getting max value from his overpairs is much better than getting max value from his bluffing range, since I do not believe his bluffing range to be wide at all. We are deep, so assuming i x-c the flop, which I can easily do with AQ, QJ, JJ, honestly even QQ I do not think from my own experience that players will shove 500$ on the turn as a bluff. So id definitely say its better to go for value than to wait for a bluff.

Hey Zljko
What do you mean here ?
"Either way, as long as its a board with a lot of draws he can never fold, in fact you do not need to have any bluff raises and you will still end up allin vs KK AA. "
You mean as an exploit people never fold KK+ in that spot ?

Yes, in these positions they will never fold KK+, at least I know they will never fold vs me. I also cannot think of a player against which I would fold KK there, actually I can think of 1 or 2 which is extremely rare.
So I can use that to my advantage, and raise everything for value, knowing they will always call KK+ and only fold a bluff which is okay with me.