Admittedly, I am not one that typically finds paid mentorship very valuable, but I also respect that my degree is in business with a focus on real estate, and my first job out of college was in real estate (so it is a little hard for me to take my 20 yrs of knowledge and rewind it to try to view mentors from a completely fresh lens).A couple points: I view mentors, especially these expensive ones as a catch-22. 

Im only thinking about doing this because I think he wants at least 400k.Does that sound like a smart plan?

A LOT of people don't have that planned out.

do you cash flow in month 1 if your rent is $1200, and your expenses for that month are $1198? 

So if the house is worth 300k and you owe 200k then most you could pull out would be 40k (minus costs) and it would be a second mortgage most likely which would be expensive. 7.5-9.5% likely.But, you can put as little as 15% down for a conventional loan on a single family.

I've lived there for all of a week, and am already planning on moving out in a month or two. 

You reduced the amount of untaxed capital gains you’re carrying forward but you didn’t create an expense or a deduction today.

This may come into play as you near the end of life and need to think about estate planning.4. 

My 13th hour cancellation was someone who had booked for 3 weeks and after a week announced that her plans had changed and she was leaving the following morning.

You get a deduction for the contribution, the gains grow tax-free and as long as you use the proceeds for health-related expenses the funds come out tax free as well.