89o busted draw

I don't like your flop line. you started with 1k and by flatting flop you have put in 300 (1/3 your stack). you should make up your mind on the flop and either semi-bluff shove or give him credit for a huge hand and fold. what you decide depends HUGELY on your dynamic with this reg and how aggro he is. if you were deeper I think flatting is much better on the flop.

As played, I think you can still represent some strong hands like 2 pair or sets so I don't mind the river bluff. Again, this does depend a lot on the dynamics you have with this guy. If you have been messing around with him before he might be suspicious of this line.

It's just an odds call though, isn't it? I'm much more concerned with the stack sizes on the river. If I make it as much as I made it, can I get him off a decent T?

If villain is raising Tx in flop he should be planning to stack off with it versus 3bet. Turn and river are basically blanks. So I doubt he is planning to fold his Tx in river. Personally if I would try it I would probably go for shove. But might be he is calling anyway.

Only thing we can get him to fold might be some air or same sort of busted draw we have. For that small bet is enough. Though I would think straight draws are more likely to just flat from position in flop.

You don't get direct pot odds to call in flop as free river is quite rare to see, but with implied odds it should be fine imo.

if you are trying to get him off Tx on the river then you should just shove and rep 2 pair+. he is never folding Tx to this size imo.