I've been stewing over a few hands that I lost after being way ahead. There are a few side-themes involved, but the overall question I have is regarding raises OTF when I know I'm ahead. Example...

From button with about $100 at a 1/2 table, I call a loose/tricky player raise to $8 with 56.

Flop 668
Villain bets like $8 I raise to $25. He calls.

Turn is a non-heart7. He checks. I check. I don't know why I check. Please help me understand what I should have done besides check.

River 4
He moves in.

I played this hand poorly on pretty much every street, including pre. But I'm most confused about how much I should have raised OTF. If i shove, and he folds, is that good for me? I win like $25 with trips.

Next hand...
UTG raises to $8, and I suspect a high pair. MP calls. I call with two red 5s.

Flop is 57T two diamonds.

UTG bets $20 MP calls I raise to $50. Call call.

Turn is an 8. Check check, I shove for $90. Snap call. MP thinks a while and calls.

UTG had 88. I threw up a little in my mouth, and wondered where it all went wrong.

Moral of the story don't I want calls when I'm ahead? Should I have raised more with either hand? Bad luck and move on, good bet size? Idfk...

Well let me ask you this; what is your image according to this player? Does he view you as tight or loose? If he is loose/tricky does he barrel post flop light or is he just loose and tricky pre flop but more straight forward post flop? If he is loose post flop as well and is not thinking in terms of ranges (he should not be betting this board often oop as it will miss him often) then I think there is great merit in just flatting the flop and letting him barrel. The pot on flop is roughly about 16 bucks? There aren't many if any turn cards that will keep you from being committed on the turn when the pot is 32 with 84 behind and scare your villain from continuing his aggression as well as denying him any info on how strong your hand actually is. If he bets anywhere close to pot on the turn then you have an easy shove for value. If he is more straight forward though and won't barrel off after you call the flop then I think raising for value is fine and I think your raise sizing is just fine. On the turn the pot is now 66 and you have about a pot sized shove left and that is what I think you should do for value. Your opponent could easily call with 99+ and pair+draw hands like 97s, 87s. I think in the 2nd hand you just ran into some bad luck, however I do think your raise sizing needs to be larger on the flop. Once the preflop raiser makes it 20 and MP calls I think a standard size is at least 60-80 with closer to the high end of that being optimal so you can discourage them from drawing somewhat cheap on a wet board. I didn't see any stack sizes in the 2nd hand but if you were somewhat shorter stacked again then shoving may be the best move as well. Hope this helps and good luck next time out.

H1: fold pre. suited connectors work best in multi way pots and when your implied odds (risk/reward) are high. The logic here is that the poor equity you have vs the raising range of villian pre is offset by the expected money you win when you flop big and get stacks in. The bigger the stacks, the more this is amplified. 50 big blinds is no where enough to be calling with this PF. Remember: the first factor to consider when starting a hand and how to play/approach it, is your stack; and the stacks of your opponents. Stacks mean everything. Flop is fine with the limited info you provided. Turn check is horrendous, and worse than the flop call, as you are giving any flush draw/9/overpair a massive freeroll. The pot looks to be roughly $66...and you have $67 left. Easiest shove ever. Always ask yourself what your actions are achieving. What does checking this turn do for you? Your not slowplaying, your not pot controlling, your not taking a free card. You have a very strong hand with a pot built, time to get it in.

H2: Cooler, nothing you can do. Hand was played fine from what i can see.

The PF call and turn check in hand 1 are two fairly glaring mistakes. But good for you on coming to a site like this to find answers. Keep asking for advice, stay objective, and keep an open mind, and you will plug those obvious leaks fairly easily.

Sorry, just realized i misread H2. Didnt see that there was a call off the 20 bet. Your raise for sure needs to be more than to 50 here on such a wet board to protect hands against the many draws that can be out there. If the flop was A 9 5 rainbow, there would be a lot more merit to the small raise.

In hand one I'm assuming the other 8 was a heart?

The preflop call is marginal to bad as others have said. Short stacked your hand is really just 6-high. You need to stick to hands with have greater absolute strength like high cards and good pairs.

The flop raise is good. Villain has plenty of hands he can continue with. You've hit a very good flop for your hand and should want to stack off. A lot of V's will expect you to slow-play because that's what they would do and they'll pay you off.

I'd for sure shove the turn with only a pot-sized bet left. We still get value from worse. Giving a free card to flushes is bad and you're missing value from overpairs which won't call when a scare card comes in (like the 4h)

On the river you have to fold. Most villain's aren't sick enough to turn overpairs into bluffs so V's range is almost solely flushes and full houses.

In hand two the call pre-flop is a bit marginal because you're still a little bit shallow, but probably good enough.

On the flop you have a bit of an awkward stack size. The board is pretty draw heavy and you don't have much behind so I don't mind shoving. You can also make a baby raise like you did as long as you realize you're committed on 100% of turns. I don't like giving great drawing odds, but if you feel villain's will stack off much lighter with made hands this way this sizing works well. It's just a cooler, really.

You don't want your opponent's to fold hands that don't have correct odds to call. In hand 2 your opponent was crushed on the flop and he got lucky. It happens and you should actually feel good about this result when he pot committed himself drawing to two outs.

Hand 1. Fold pre. With only 50bb, we're low mid stack/high low stack. This means it will be very easy to get all of our money in ~turn. We want to get our money in with hands that pay of, not rags like low suited connectors. In general, the shorter the stack, the tighter the play. Furthermore, compare your range to villains before calling, and have a plan for the flop before entering the hand. We're going to have to hit the flop really hard to be able to continue. Considering any sort of connection is only made 1/3 of the time, and the type of strong connection we need happens even less frequently, we're going to be giving up our pf call most of the time. This is -EV. If villain was very straight forward and rarely made continuation bets and would fold to one, a marginal argument could be made for playing this, but other than that, this is a simple fold before the flop. As played I like your raise to $25, though more would have been nice just to make it easier to ship on turn. The turn is where you doomed yourself. I'd bet $50+ to make it real simple to ship the loose change we have left over on any river...

Hand 2. When calling to set mine, make sure you have the right odds. You'll hit a set only 1/8 times. I don't mind the call here, assuming we know we'll take in over $64 for the 8 we put in when the 5 flops. I think your flop 2bet is a little weak. 2.5x when another player already called isn't a great deterrent. I'd raise to $80+, which would make it easy to commit the rest of our stack. Pending what I thought of the players, I might just shove in certain cases. (What sort of range were you putting MP on?)

H1: fold pre but as played, perfect so long as you called the river.

H2: again fold pre but so long as you didnt stack off for some gross amount ott well played. you ran into the once in 23.

H1: Why are we not betting turn? Seems awful on such a wet board. It's like the check version of spewing.

H2: Fold pre? Seems like a nice spot to set-mine.

To start, a hearty tip of the cap to so much feedback. Thank you.

H1 I played badly, not just that hand but I didn't get a good feeling from my whole session. I haven't played since due mostly to bring too busy to play, but I will def play deeper. I'm learning that even though I might feel comfortable playing a bit shallow, my opponents are not as afraid to play with me because I can't put huge dent in their stacks. More on this in a sec...

H2 I did not have a good read on other player, but thought he was on some kind of draw. He flatted from mid position, and flatted again OTF, and I recognized the flop had a lot of draws. When the 8hit turn (yes I think 8) and raiser snap called, I'm like, did he have a straight draw??? But then to raise from UTG I was like, "he had an overpair...could he really snap with AA? Can I be that lucky?"...(nope. I could not.) So yeah, I recognized that MP was probably drawing, which is why I raised.

The player who made a set OTT, being right next to me, I talk after the hand, how much would he have called, he say not much more. If I make it $80, he say he would have folded. I do not know if flatter calls or not. He on the other side of the table.

So my next question regards buying in deeper. Should I worry that players will notice I buy in deeper and adjust their play? Maybe test me more? I don't want to deal with that. I play tight, and try to push in good spots, even though my examples here are me playing poorly. Many, many times, I've doubled or tripled up and at least one person not in the hand will say something like, "I didn't think you had that..." Meaning I concealed my hand strength pretty well.

Great replies. Please, none of you sit at a table with me. LOL!!!

I don't think you need to buy in deep if you don't feel comfortable and or don't feel ready to make big turn and river decisions, however as some of the others have stated you do need to realize what hands play well with certain stack sizes pre flop. Eventually you will want to be buying in for at least 100bb's because the only way your game will develop is if you learn to play deeper in and out of postion and being able to play hands like suited connectors and small to medium pp's comes along with that.