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.

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).

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.

That is the max loan to value where you can get the best rate available which will still give you 135k~ in cash for the next project, but leaving you with healthy cash flow on the property with the cheapest cost of interest you qualify for. 

I enjoy a healthy debate and learned a lot from this thread 7 months ago and continue to learn from it today!

Several of our out of state investor clients are securing very healthy terms on CRE including apartment complexes and industrial warehouse spaces with as little as 25% down and rates currently ranging from 5.5-%-6.75% on 25 year amortizations. 

We are very fortunate to have such a healthy real estate market!