Thanks for all the insight.

You all gave me enough confidence to insist he can finish this last bit up while having a part time job. Hopefully he follows through and hopefully we're looking back at all of this a year or two from now and it's in the rear-view mirror. I know there are new challenges to come, but this season as been particularly tough.

That's not how it works, you do not just get handed a commercial certificate by having 250 hours and passing the written. He will need to perform the training requirements of the commercial certificate and be proficient enough in the maneuvers to have a CFI sign him off for the practical. Depending on the training he has had so far through 200 hours, it could take him significantly more then 250 hours.

If he budgets out like 20 hours for training then I think he should be alright

He has already started the commercial training. It look months(!) to get scheduled with a DPE for his IFR, so in the meantime, he started commercial training even before he passed IFR. I know he wouldn’t be ready for the commercial check ride tomorrow, but feel pretty confident he’ll be ready at or around 250 hours.

Again, it all depends on what he has so far that could count towards the commercial requirement. But if all he has in Private and Instrument training, getting your commercial is not just as simple as getting to 250 and passing the written. You need to meet the specific requirements and be proficient on all the maneuvers.

rgr, then it should be no problem to get it by then. They way it originally sounded in your post was that all he would need was 250 and the written, and not the flight training experience.