I’ve found that for the time investment it requires, I really don’t save that much doing it myself since I’m less efficient than the pros are.

I have talked to the Hendricks County Assessors office a few times and it sounds like if you designate a property as a rental with the county they say it can (depending on the area and the current assessed value) save you money on real estate taxes. 

My backup plan is to purchase more condos (~200k/each) which gross about 45k/year (net just over half that) and save up until I can afford something bigger.Ideally I want to stay in the same city with the multi and do a combination of long term and short term rentals.Thank you for your time.

The problem is if you calculate the long term interest savings, it takes many years to even break even on the larger upfront interest payment.

Its payed for (with our savings) and we are still waiting to have the remodel completed and to get lit eased, the estimate for the lease given to us was $700 to $850.

Buy a multi family with low money down, rent out the other doors so your mortgage and other expenses are paid for, essentially you’re living for free and saving a lot of money.

Because my income minus bills is all I have as far income to grow my business, I will have to do wholesaling to save some money for my first flip and it will give me insight on FINDING a deal others missed.

My wife would not be thrilled with emptying out the savings.

I have been at the REI game since 1992, I have a rule that has saved my butt many times, you can't force a deal.

You could obviously use the HELOC, or borrow the down from your 401k, you could save cash for a down payment and get standalone financing for the new buy, or any number of things.There's plenty of SFR near you that would cost less then 165k, and I'd be tempted to use just as much equity as I needed to put a down on the first one and get it rolling before repeating the process.I wondered if you'd ever heard of the Infinite Banking Concept?