Have a family member whose health is rapidly declining.

Since then, I still do some creative finance, but also do many BRRRR which also I have to buy them at a healthy discount.

They are both healthy and don't appear to be doing any damage to the house other than maybe dropping leaves and twigs every now and then.  

That's a healthy expense.

Lenders are almost universal in their requirement that a borrower has "skin in the game".

My dream is to have the freedom to pursue my passions for people leadership, engineering, and a healthy lifestyle outside of the corporate ladder.

Let’s say the main tenant accounts for most of the annual revenue with a lease ending soon (is healthy and probably looking to resign).

Its to make sure you have enough skin in the game on this property such that when you buy the next one you're not going to be in over your ski's.Hope that helps, there are many ways to structure your situation so that you can bob and weave around these obstacles.

Since your current portfolio is generating healthy cash flow, you might benefit from diversifying into an asset that provides a mix of stability and growth.

For context, I'm in my 30s and while I'm healthy, my days of working back-breaking jobs for minimum wage and "exposure" are over.