pretty silly hand to chr with, you're going to get peeled a ton (and if you get b3b you are folding), and a majority of turns, T J Q, and diamonds are all really crappy for you. I'd imagine BTN has a lot more QdTc type hands that will not fold to your ch/r, and you'll be in trouble oop in a bloated pot on the turn. Just ch'c the flop and go from there.

I agree that this play out of position is silly, I was kind of lost, and tried getting more information. Looking back, I think the major issue is that if we get peeled, we have to check the turn and that gives him all the information he needs. 

Thank you for the advice.

Overrepping A9 TP hand range with the C/R flop.

I'm not a huge fan of your preflop defense, you don't need to get in that kind of spot in 25NL. Keep very strong ranges OOP and your life will be so much easier.

About your flop play, agree with mplecki23.

You should pretty much never defend the SB with A9o, because your hand can't draw to a straight/flush, you can easily be dominated, your hand plays poorly when you miss.
3-bet or fold.

What are you trying to accomplish by check-raising? He's going to fold all his worse hands, raise/call with hands that beat you, or have a ton of equity.

What's your plan when a diamond hits? How about an offsuit king? You'll get in big trouble on most turns and river, and you'll be OOP in a bloated pot.