Nothing to be embarrassed about, I’m sure this is a spot many people struggle with. It deals with one of the fundamental differences between deep-stacked and short-stacked play: with a deeper stack, you need to be more concerned about protecting your stack and avoiding tough decisions or putting in a big chunk of money from way behind, rather than protecting your equity in a pot that is small relative to the effective stacks

Raising the flop is the first mistake. Although I can understand why it’s tempting – you’d like to fold out overcards and a few worse hands will call – you are not likely to be ahead of Villain’s range for continuing to your raise. In other words, although you gain something from your opponent’s folds, you are putting money in bad when called (even though you’ll occasionally be ahead). When you put more money into the pot, you strengthen your opponent’s range. She will fold her weakest hands – the ones you’re furthest ahead of – and her range will become strong enough that you can’t be excited about putting more money into the pot. That’s not such a problem with shallow stacks, because you can just get all in on the flop without risking much relative to the pot, but here there are still two more streets of betting to go and by raising the flop you set yourself up for a lot of bad spots when your opponent doesn’t fold. (And if you’re really just hoping for a fold, then you’re bluffing and it doesn’t matter that you have 99 – in fact the 99 is a liability because it has few outs against your opponent’s continuing range).

Betting the turn is essentially the same mistake, and calling the check-raise is a disaster. At this point all you can beat is a bluff, and although it’s not entirely impossible that your opponent is bluffing, you are so far behind her value range that you still can’t profitably call. Not to mention that even if you do call, she can still keep bluffing on the river, at which point you end up folding anyway.

You mentioned in a previous thread that you were concerned about getting exploited by aggressive players. It’s quite possible that in spots like the turn here you have too wide of a bet-folding range. However, folding fewer hands is not the only or best option. What you need to do is get to this spot with fewer marginal hands in the first place, which means not raising hands like this one on the flop.

Basically, my guess is that you are overvaluing protection, which is not generally a very important concept in deep-stacked NLHE. There are worse things than getting drawn out on or bluffed out of a small pot, and this hand is a good example of what can go wrong when you focus too much on protecting your hand rather than protecting your stack.

More good questions. You really just need to let go of the idea of finding out “where you’re at”. I know it’s a common thing for people to worry about, but, as with a lot of the so-called wisdom passed around the poker world, it’s incorrect. Poker is a game of incomplete information. It’s about making the best decisions you can with the information you have. 

You have a lot of information, even at the moment that you are facing the flop bet. You know that your opponent raised in early position, which gives you some idea of what sorts of starting hands she could have and which she probably will not have. Then you see the flop, and get some very important information, which is that many of those starting hands, such as AK and AQ, did not make a pair. Then she bets, which may not give you much information, as betting most or all of her pre-flop range could be defensible here. 

Your job is not to figure out whether she has AK or AA. It’s to make the best decision you can given that she could have either. Folding is no good, because you are getting good odds to call. It’s OK to call and lose to AA sometimes, because you’re compensated by the times you beat AK and by the money already in the pot.

Raising is tempting, because it would be nice to make your opponent fold AK, but the downside is that if she has AA you are going to put in a lot of money drawing nearly dead. Not to mention that she might not fold the AK anyway and could end up bluffing you out in an inflated pot. 

That leaves calling. It’s got its own downsides – your opponent could draw out on you, or she could successfully bluff at a scare card even if it doesn’t improve her – but it’s still better than the other two options.

Again, poker isn’t about perfect information or perfect options. What happens too often is that people simply say “well if I call she might draw out on me” as though identifying the downside of a particular play is all it takes to rule out that option. You have to weigh the advantage and disadvantages of each option and find the one with the highest expected value.