So in some ways it feels to me like 2005-2006 again, but on the other hand the developments move much slower and much more deliberately.

I can't imagine all you need to learn both about the medical side and the business side.  

If you look over the last 5 years of appreciation rates and compare them to an area like nashville  you will see your area more then likely has appreciated at a much slower rate.   

You could then take out a loan and gift him money each year up to $14,000 per year to cover medical expenses if needed however interest would not be deductible as it was not related to the activity. 

Your money now is not serving much value and would be best distributed among several properties in the form of minimum DPs.Taking a HELOC and paying it back to reuse again is a much slower process that has no advantage.

But I believed you nailed at the right approach( income & slower growth). 1031 exchange your property & use the $400K, buy & Hold 4-5 SFH outside of CA. areas that will net you 1% rental return on your $80-90K homes.

Nicer 2 bed / 2 bath condos in Scottsdale are now selling for around $250k-$260k or more. 3) You'd obviously be living in the condo during the high season rental months, and then trying to rent it during the slower summer months.

I’ve been looking in the energy corridor to the west, Spring near Exxon, and to the south in good school districts and near the Medical Center. 

Part time and dual career never scared me and many of our agents (full time 911 operator, full time medical device sales, full time mail man, etc.) made more than $100,000 a year selling real estate while others made the same flipping homes.

It could result in slower sales on commercial properties.