I have significant enough assets and capital that I can make a few loans while still maintaining a healthy stock portfolio to keep my money working for me. 

That's pretty healthy.

If you are looking for cash flow + appreciation South Eastern Wisconsin is booming with industrial growth and healthy rents. 

Most lower priced condo projects are not very healthy and why they are low priced.

So, my first caution is it would be healthy not to expect similar results on certain real property investments/deals in the current and near future cycles.That said, there are multiple considerations and clarity needed, before I would act on any investments with your equity.

I invest in military towns because they're usually lower barrier of entry and healthy economies.

Even if a title company were to manage the setup making sure all parties are paid, the cheap debt and cash flow would not be enough to be enticing to any investor even if midterm rental could yield a healthy return. 

The community is also a wonderful place where we help each other win - along with some healthy competition.

I'm feeling for this guy and his wife's health. I

There is a healthy amount of leverage, but the whole point of investing is to grow equity, and eventually a return on that equity.