"Kelly Neville" wrote in message:

At 9:00 he is
let out to go

Is he let out or are you taking him out, on-leash, to his potty spot? Do
you use a cue word to let him know what he is expected to do (like 'Go
Potty' or 'Go Pee'), and do you tell him when he's done good ('Good Pee!')
and praise/treat?

If he didn't go during one of his outings he would be put back in his
crate
and let out on the hour every hour until he went.

So, at what point is he messing? While he has free reign for 2 hours?
Personally, I would give an unhousebroken dog NO free reign at all. The dog
will always be tethered, confined or under direct adult supervision.

Suja