Would you rather be in debt up to your eyeballs just waiting for the day you can cash out or would you rather be debt free and add on an additional property as funds allow to supplement your lifestyle? 

Another benefit is the ability to pull supplemental loans versus full refis (pro or con depending on where interest rates move).The main objective is weighing these pros and cons of each.  

Additionally, I will be working as a Life/Performance Coach to supplement my passive-ish income from REI.

This helped me and my wife define what we wanted to do (5K per month of rental income to supplement our existing retirement plan) and how we wanted to do it (do not put the existing retirement plan at risk).

We supplement it with a few extra pages of application,We were disappointed that it was a slower response time, up to two days and always many hours.  

The Self-Sufficiency Test does not pass the requirement (PITI ≤ appraised rent x 75%).I got in contact with another Lender B who is telling me the self-sufficiency test is required only when you need the rent pay back to supplement your income as qualification for the loan.

Are you looking for long-term generational wealth or just some sidecash to supplement your current salary?

I’ve been a real estate investor since Moby Dick was a minnow, and I've been satisfied with the 7K supplement to my military retirement.

The real problem is is I have no defined goal do I keep and let this little house supplement my income in my later years, cash out,invest elsewhere.

While you are occupying the property your mortgage is being supplemented by the income income from the other units even though you are not cash flowing you are making money as a form of savings .