Live 1/2, local casino, mid-day. V is an old lady, very passive, very fit or fold, basically plays her hands face up. I think I had the perfect situation for stacking her here, and I didn't get it done, so this is basically a bet sizing question. On to the hand...

Effective stacks ~120, as V is short. V limps in EP. I have 65ss in the CO and raise to 10. I want to get heads up IP against this V with this kind of hand. I think she will limp-call a lot of hands that will flop a lot of mediocre top pairs and stack off when I hit my straight or flush. And if she hits, she'll bomb the pot and I'll have an easy fold. Like I said--she plays face-up. All goes to plan pre-flop. Button and blinds fold, V calls, and let's see a flop.

Pot ~20 (after rake). Flop: 9 3 2 (rainbow). V donks $6. From this V, this is a weak top pair all day long and twice on Sunday. Easy call with my gutshot. Implied odds are plenty good, and this is the exact scenario I was looking for with this hand.

Pot ~30 (after rake). Turn is an offsuit 4, and V leads again for $6. I call, looking to raise river, obviously.

Pot ~40. River pairs the 9. V leads for 10. I raise to 40. My plan all along was to stack off in precisely this scenario, but now that we're here, the pot is too small for the remaining stack sizes. Or so I thought at the time. Now, I wonder. Pot is ~50 after her river lead. She's got ~90 behind. So my raise to 40 is about a %60 pot raise-pretty standard, whereas shoving is about a 1.6x pot overbet.

V calls the 40 and shows a 9. I show my straight and take it down. V says she would have folded to my raise had she not gotten trips on the river. So I win a medium-sized pot, but I can't help thinking I got exactly what I wanted from this board and yet didn't get all her chips, which is what I was after when I raised this hand pre to begin with.

Thoughts? Should I have raised turn, setting up the river shove? Should I have just shoved the river anyway when the top card paired?

From what you described about villain saying after the hand was done, seems like you weren't getting any more money from her anyway.
But, that's being results oriented and besides the point. If you're going to play a small suited connector like that, for the reasons you stated, of course you have to raise the turn. Otherwise, don't bother playing that hand. You got really lucky you made your gutshot.

The reason to isolate a V like that 60bb deep is not to stack her with straights or flushes. It's to win the pot with a cbet the majority of the time. The draws are plan b.

Def raise turn as played. I'm not confident you're stacking this V very often regardless, though.

I think your thinking is flawed relative to this hand in every possible way. Most confounding is how you don't raise the turn.

Like Jay S said - making hands isn't how you beat this type of V. You make money when they miss.