Once rental income is enough to supplement a comfortable lifestyle and still be able to put away large amounts of capital while working W2 with less hours or getting into real estate sales.My big question is grind it out here and save (invest) 50k annually on the road with this crazy W2 job.

http://www.ocgov.com/gov/assessor/realproperty/supplemental  This is assuming the property is located where you live of course.

I would like to keep it and finally use it as a supplemental source of income which doesn't seem possible now.

I have done my due diligence of googling and youtubing information but I would like to supplement it with real life experience from successful investors like you.

Also, and most importantly, it will supplement his current monthly passive income.  

Between the military, task apps, new business, etc. there is never a better time to be able to make supplemental income and be my own boss.

I plan on doing a buy-improve-hold strategy to build equity and passive income to supplement my military pension in 8 years. 

However, he still wants to hold on to that property so that he can rent it out and create residual income to supplement his current income.

I am now a professional licensed engineer and I am also able to do real estate and investing on the side to supplement my income. 

Find a bank that has a higher limit or supplement some of your own money.