Originally posted by TwiceT
Thanks for all the comments
You mentioned many important points, good stuff! 
Most of you analyzed the hand from the perspective "how it should play out" and didn't discuss "how it has been played". Furthermore, most of you broke down ranges and went into what-if scenarios with both players ranges, a discussion on betsizing didn't get started though. When I look at such a hand, I would suggest to discuss it from two perspectives. Firstly how the hand has been played by Hero, secondly how the hand could/should play out.
Assumptions: Villian is unknown, we know some regulars on that limit and the fact that we have 0 information on MP leads us to believe that the odds are in favour of him being not an experienced reg on this limit. MP has a 180bb stack which at least tells us we are not playing against a SSS or MSS player.
Preflop ranges in both scenarios are the same, you talked about preflop at length already. I would say a tag has a ~ 10% calling range here consisting of: 22+, ATs+, KJs+, QJs, JTs, AQo+ A random fish can have pretty much anything, even A7o (30% range!?)
I) As played by JB
Flop: JB bets 2 into 3.75 - before moving ahead and discussing calling ranges we need to realize what such a small betsize does to Villain's range. There is a significant difference between a 1/2pot cbet and a 3/4 cbet. A-highs, K-highs, gutshots, lowest pockets might call to 1/2, but fold or (semi-)bluff raise vs a bigger bet. Its not villain who plays his range only, its our betsize that influences how that range is going to play to a big extent as well.
"I'm really targetting flush draws and 89s and hoping to get paid off if he hits. I think there's a limit to how much I can extract from him if he has some mid pair or overpair, which is his most likely range for calling on the flop." You yourself say you are targetting FDs, OESDs and pockets mostly. What you do though, is target a much wider range by betting half pot. If you'd say "I want to target the widest possible range to let him float the flop ... " your betsize is consitent with your statement. However, if you target the range you want to target, there is no need to bet so small. Bet 3/4 and really target those hands which are not folding to one bet anyway. 89 or 55 (the weakest hands of the range you target as you say) don't fold anyway. The other part of his range doesnt either. Before we bet the flop though, we need to have a plan. With your logic of hands you want to target, I would say a good plan is to bet bg on the flop and small on blank turns. No hand you mentioned will fold the flop with is the reason for the bigger flop bet. On a blank turn Villain might fold his range to a bigger bet though. By betting small we allow him to i) bluff raise and ii) call light ip in order to draw to the 2nd best hand and pay us off. In most cases I would also bet small on R not even thinking about the cards for now in my general plan, simply because a big-small-small approach on this texture with our assumptions maximizes our EV vs weak pairs who take the odds and call as well as maximizes our EV vs hands who want to bluff and read our sizing as weak.
Now that we have a general plan before betting on the flop, we are set to dive into postflop. JB decides to bet small on the flop and gets called. Turn is a "scare card" and one we would bluff frequently. I think going ahead and betting small again is a solid option. We lose a little bit of value vs A-highs with a small turn bet, but we maximize vs lower pairs and increase the chances to get bluffraised be the gs floats like J9. Also spades-floats can easily call and draw to a 2nd best hand. The fact, that we slightly lose value on the turn vs A-high is not so critical though because after a small-small approach on F and T we should bet big on the R. Reason being is, that the weak part of his range cannot really bluff catch R now since after the line we took we too often have a hand that beats him, we mostly get folds anyway by 88. FD, OESD that didnt bluff till now, probably wont bluff the R either, so we also dont have to attack those hands (check-call is an option you might think, I do agree, a viable option because Ax bets anyway and busted draws might bet too). We dont block Ax combos which is great, so we target all the Ax hands that floated F and called T. A decent part of Villain's range as most of you discussed earlier already. Hence, betting R bigger after going small-small before is a solid idea.
JB had a different plan though with which I disagree. He went small-check-small. I would even argue, that he didn't have a clear plan on the turn what to do after he checked vs different kinds of betsizes from MP. Now that MP checked back, we can assume he doesnt have Tx ever. We are looking at 22-99, K-high FDs, sometimes Ax being a bit deceptive and potcontrolling. Against this range, I dont see any reason to bet. Now on the R it is really obvious "that we had hit our A on the T and didnt want to force our opponent away". T is such a good scare card, why would we not bet T but bet R? Villain can easily fold weak pairs and K highs, and call Ax. Ergo: we should not bet imo, but check again (JB - remember the hand from our book????????? "checking twice, I didn't know that was an option ...."). We should go for a check-raise, expecting Villain to check back pairs and K-high but bed busted draws and especially Ax. Our line is quite goofy in Villain's eyes so you will mostly see Ax tank-call our check-raise.
II) How I would appraoch the hand
Given the limited information and the flop texture, I see three lines worth taking. I will try to briefly cover all of them.
1. check/raise - bet - betAI
This line targets pairs that bet the flop when checked to (most of them I'd assume) and then feel like getting bluffed and not believing and calling one or more streets. Ofc it also gets the money in vs Tx, but we don't need to focus on those combos too much as we always get it in anyway. This line is especially powerful vs weaker players since they have a hard time letting go pockets on that board, especially 88+. Against a pocket pair heavy range this turn card would be bad, because it gives us quite some fold equity. I would bet the turn small and mostly focus on Ax of clubs and the occasional JJ that still don't want to fold. I think at that point we lose our customers 22-66 every time and 88, 99 mostly. We don't gain much by checking turn and betting R, its too obvious that we don't want to scare these pockets away on T and value bet R. In any case, I would shove the R, expecting to only get called by Ax(mostly in clubs) or Tx. That's fine, checking doesn't accomplish much since Villain more often has Ax than busted clubs which want to bluff.
2. bet - bet - bet
This line has been discussed the most so far. T is a good bluff card and since we would bluff here with all FDs, OESD, GSs we want to value bet as well. 99 might still call one, all (broadway floaty) spades combos call anyway, all Ax call. We only fold out all the small pockets and floats who now dont dare to bluff raise. On the river we just bet again and dont expect Ax to fold because both FDs are busted. I would not fold against a raise ever, especially if we bet on the smaller side. Villain can very well put us on a AJ, AQ, AK value bet and try to raise us off it repping a FH with his busted OESD, FD .... or even turning a made hand into a bluff (99, JJ).
3. check/call - check/call - check/raiseAI
JB said we have no reads, no hands on our opponent. Still if we played a few hands vs this opponent, we could have picked up on one hand he played before or one tendency. Maybe not a read already, but having the feeling MP is slightly aggressive makes me consider this line. By checking the flop we immediately reverse our range and put MP into the driver's seat. I would argue almost all hands would bet, especially pockets for protection and all (also weak) draws for fold equity. A-high will check back regularly, especially AQ, AJ for decent enough showdown value. If we face a bet we check/call representing A-high our medium pairs mostly. I would continue representing a weak range all the way to the R and c/rai. Our range looks "face-up" after being PFR from UTG and then check/calling 2 streets postflop, many aggressive players would just bet-bet-(overbet)shove as a default (TwiceT in 2009 would have done exactly that).
I can already picture JB jumping out of his chair at uni and asking "But what if MP checks back F? You didn't think about that hah?". I did sir; easy answer professor: Our range assessment still holds true, the range just clearly shifts to Ax hands. Those would call pre in those positions and often not bet on the F. Since the turn is an A we don't need to bet as Villain will bet for us. We can then decide whether to check/raise (I like it because its unexpected and players don't fold Ax here ever) or check/call and represent a weak Ax. Again, I see JB pointing the finger and saying "What if MP doesn't bet the T? You didn't consider that option hah!". Ofc I did sir; Now we have to think about what it means if Villain checks back 2 streets with our range assumption and what our range looks like to him. We clearly look super weak, 99 being probably our strongest hand here in his eyes. MP still has low pockets, those might call a very small bet. He might still have Ax quite a bit where he thought he can only get one street of value and wanted to delay to the R and maybe spike a bluff or just value bet himself. I would therefore check/raise the R big and represent a bluff and represent the fact that "I know you know I have nothing, but I know you have nothing as well so I bluff you and you cannot call".
Before JB jumps at me asking "What if we check/call F and villain checks back T?" The A is an interesting card. We could very well have strong A-high and check/call the F. However, what is the point in betting R? We represent AK, AQ way too much. I rather continue representing 7x, 88 etc. As a consequence I would check the R to MP, knowing that he would check back 99 but also knowing that we don't get him to call anyway given the previous actions and the board texture. Often enough though MP will bet A-high on the F and then be surprised to have hit an A on the T and snap check back. Once we check the R again, he will most likely bet and we can again make a funky check/raise that will confuse the shit out of Villain, mostly resulting in him calling just to see whats up.
There is merit to all the lines. Which one to take depends on our opponents. Whenever we have no stats, we need to make use of all other infos out there. Even without any info we should still have an idea how the game is been played on this specific limit on that specific poker room. Be aware how the betsizing of both players massively influences ranges and influences our decisions. We will mostly play against opponents we have some notes/stats on, that's why it is important not only to consider all our options but also finding the best line vs each opponent while not neglecting to have balanced ranges in most spots.