This doesn't sound like sober behavior. If he's serious about getting well, maybe he should begin working a program of recovery like AA, Rational Recovery, AVRT, SMART, Life Ring, SOS.....
Sounds like he's really seeking help with finances, maybe??
What's your gut say?
If he were sober, he'd be working on himself and dating you--taking you out, etc and winning you over that way, like a sober person would do. maybe. I dunno.
just some thoughts