No, it's not budget related. The flying money is coming from the sale of a property we owned, so that money is there for his use. It's the money to live off of that is of short supply.

However, he definitely runs into scheduling issues. His flight school needs more planes. They book up fast (as do the instructors), but I feel he could get around this and he hasn't. (He needs to book more flights per week and book them further out in advance.)

One example is, right after he passed his instrument, he didn't have any time on a plane for almost two weeks! I'd asked him to book time out for after the checkride, but he said he needed to pass the IFR checkride first and then he'd book time for commercial training, but he couldn't do it beforehand, or it, didn't make sense to, or it just "isn't how it's done." I'm pretty sure he could have booked it in advance, but it's hard for me to argue with him because he just says that I don't know what I'm talking about... which is true. I don't. So, that's why I'm poking around here asking questions. :/

As far as the job at 250 hours, we're planning on selling his soul to one of the little charters that hire at 250 (with a 2 year contract). I know those can be controversial and the pay is crap (but hey, we can only go up from $0), but I truly cannot imagine the stress of trying to also carry him through a CFI rating after the struggle it's been to get through commercial in any sort of timely manner. I just can't.

I also don't think he'd be good at managing his schedule, or managing the schedules of students as a CFI. He needs a boss telling him when and where to be.

He's a good worker and he's a good pilot. He's gotten high scores and praise on his tests/checkrides so far and from his instructors. But he's just not excelling at this self-directed schooling model and I am terrible at standing by and signing checks while feeling like I would do this all so differently (and much quicker).