If you decide to take this kind of route, it's still very important to go in with a secure plan and also have at least 6 months of reserves. 

I think I will need a car and an office space in the first few months itself.

I borrowed $110K from a private lender for the purchase and self funded the repair of the offices. 3 months later, I rented 6,000 sq.ft. of office space to a corporation for $21,000/month + utilities for 5 years with another 5 year option.

We're planning to purchase a long-term property every 6-12 months and sprinkle in 3-5 short-term rentals within the next 5 years!

Thankfully, my wife is still working, and we have a few months’ worth of emergency funds to cover our expenses.

I spent around 12K with his competitor over the course of 10 months and got nothing but frustration to show for it...

The property was cash flowing almost $1,000 extra per month but it is sucked into all these extra repairs. 

The tenant pays a monthly premium and keeps an active bank account and credit card on file.

Thus, my taxes should be higher because of the income I generate.If I pay off the primary, I'll increase the amount I'm able to save monthly not having the mortgage, while also keeping the income generation lower on the rental because the mortgage remains open.Any thoughts would be appreciated! 

Maybe if you are doing several transactions a month they would look at it.