I have done this overpush about 4 times and haven't gotten a call yet. I am wondering if I am picking bad times and I should be value betting more, or I have just been unlucky.

The Fast and the Furious 10475227-158241 Holdem No Limit $0.50/$1
[Feb 12 02:51:09] : Hand Start.
[Feb 12 02:51:09] : Seat 1 : rickybobby1 has $20
[Feb 12 02:51:09] : Seat 2 : KaNineOff has $10.50
[Feb 12 02:51:09] : Seat 3 : gerry58 has $105.45
[Feb 12 02:51:09] : Seat 4 : EatTheCat has $113
[Feb 12 02:51:09] : Seat 5 : IdiotVig has $540.72
[Feb 12 02:51:09] : Seat 6 : kcj77 has $48.03

[Feb 12 02:51:09] : EatTheCat is the dealer.
[Feb 12 02:51:09] : IdiotVig posted small blind.
[Feb 12 02:51:09] : kcj77 posted big blind.
[Feb 12 02:51:12] : Game [158241] started with 5 players.
[Feb 12 02:51:12] : Dealing Hole Cards.
[Feb 12 02:51:12] : Seat 4 : EatTheCat has

[Feb 12 02:51:14] : KaNineOff folded.
[Feb 12 02:51:17] : gerry58 called $1
[Feb 12 02:51:24] : EatTheCat called $1 and raised $3
[Feb 12 02:51:29] : IdiotVig called $3.50
[Feb 12 02:51:29] : kcj77 folded.
[Feb 12 02:51:31] : gerry58 called $3
[Feb 12 02:52:02] : Dealing flop.

[Feb 12 02:52:02] : Board cards
[Feb 12 02:52:04] : IdiotVig checked.
[Feb 12 02:52:05] : gerry58 checked.
[Feb 12 02:52:11] : EatTheCat bet $6
[Feb 12 02:52:13] : IdiotVig folded.
[Feb 12 02:52:15] : gerry58 called $6
[Feb 12 02:52:16] : Dealing turn.

[Feb 12 02:52:16] : Board cards
[Feb 12 02:52:21] : gerry58 checked.
[Feb 12 02:52:29] : EatTheCat bet $12
[Feb 12 02:52:13] : gerry58 called $12
[Feb 12 02:52:14] : Dealing river.

[Feb 12 02:52:14] : Board cards
[Feb 12 02:52:20] : gerry58 checked.
[Feb 12 02:52:24] : EatTheCat bet $91 and is All-in
[Feb 12 02:52:32] : gerry58 folded.
[Feb 12 02:52:33] : EatTheCat wins $46.75 as the last player standing
[Feb 12 02:52:35] : Hand is over.

Gerry was your typical CS. Is this not a good time / board for an all in push, did I just give an overpair too easy a fold?

A CS would never fold an overpair here, he was prolly chasing with overcards or somehow found it in him to fold a baby pocket.

I think he had a PP lower than the 9's there. I think you should valuebet this river instead of pushing it. 1/2 or 2/3 pot or something he can call off with his weak holding.

This is a bad time for the overpush, it works best when it looks like a bluff. This is a value bet river not a good time to overpush. If he is the PFr it might work if he has an overpair but in this situation you have to think about what he could have he might call with. It doesnt look like you were on a draw, and are trying to steal, this looks exactly like what it is, a player trying to get paid off.