As played it seems fine. If they have flushes that would call a larger sizing they’re probably putting them into a x/r range so you’ll capture that value anyway or they’d barrel river. I wouldn’t raise turn. You have the board locked down and they have an uncapped range and you kind of do,, so population might overbluff a lot of rivers. I would consider betting flop though. 1/3 sizing makes sense. You want to begin to build pot and get value from 8x and the rare 9x, plus sd and fds.

Bet flop on the small side, like .$35 to .$40. Both will have some 8's in their range, both will have some FD's in their range, UTG is 100% uncapped and has 30 overpair combos that aren't folding, this is a good board to CR bluff sometimes, etc. If they overfold this spot, I wouldn't stop value betting but I would start increasing my bluffing frequency.

Turn seems fine. I think you would raise some 8x here so I guess some kind of small raise would be ok. Maybe at a low frequency. Still some FD's that could be incentivized to call. The calling range is much more narrow since the 4 doesn't complete any straight draws.

River I think you can bomb it. The FD they had on the flop comes in, 8x can call/raise strong over pairs might view it as bluffy, etc. Maybe something like $2.9 to $3.2 as played?

I'm usually betting flop but don't mind the check. On the turn, I think we usually raise. Snowie prefers small raise sizing. I was surprised but the EV difference between checking and raising is smaller then what I would of expected (Snowie). That being said, I feel 99 lose too much EV vs both flush draws and 8x when we don't raise. Finally I'm pretty sure the biggest mistake and EV lost in the hand is the river sizing, we need to go bigger.

Betting into two players on the turn shows significant strength (or a bluff). So raising seems good. But calling IP and allowing him to bluff again on river doesn't seem bad.

As played, I would go bigger on the river. The river is good for BB's range: he can have diamonds and stuff like T7s, while you probably don't have too many of those. Also, if you had diamonds, you probably would have bet the flop, so if you bet river big he might think that you're bluffing.

Grunching.

Snowie calls this spot with 99 100% preflop, though 3betting is probably an option in practice.

OTF: being last to act and having the flop be so draw-heavy means I think we can get away with betting here. We're stabbing much wider than FH+ imo.

As played, I don't feel strongly about calling or raising turn. However, I don't follow your reasoning. If you think they're strong, you should raise because they can stand it. If you're worried about quads here, you're off your mental game. Villain has a worse hand most of the time. Deciding between calling and raising here should be a value/balance question, not a question of caution imo.

OTR as played, I'm inclined to overbet given your passivity so far and the busted draws in your range. I don't know that we'd be perfectly balanced in doing so, but that's a question for software rather than my human brain.

I just don't know that a small bet gets called significantly more often than a large one given the action and texture.

I read all comments, plenty of things said here. To not copy anyone(or rewrite same stuff) will just say: betting small flop is the way to extract more value. Nonetheless it is almost always guessing game which approach(line) will be max value

One thing I'll say about the turn raise is that it does look bluffy after you just check the flop.. What do they put you on: floated 44? prob not.. only 98s and 88,99 (for value) IMO. It might not be best for our range in theory tho? I guess this is only good in practice when you know they're solid hand readers.