Certainly trying to build something sustainable! 

I know I am overthinking this too much for the current stage as an investor, but I'm trying to work backwards from my end goal of owning 100 units.

Depends on so many factors: - What it yields- What you're trying to achieve- What headache factors you're willing or not willing to have - What tax implications come from selling (and if you have to replace your debt in a 1031 exchange)With 1.7-1.9mil that would be a 6-10 unit out here in Reno, NV that with cash could produce probably a 6-7 cap with upsides in rents. 

I know this thread is two years old, but I'm trying to figure out the debt vs free and clear debate. 

The idea that you can build wealth without putting any money into it is a recipe for disaster and the sales pitch of gurus trying to steal your money.

Resulting in lower quality construction and/or higher pricing to try and match them.   

If someone tried to charge me $75 to APPLY to rent their place I would move on.Are you getting these requests off Zillow "so and so has requested an application".

I want to understand what benefits it truly brings since seems like my insurance probably would go up after they get transferred.Another reason I'm looking into this is because I've been trying to add my Property Manager as additional insured, but my current company (Citizens) won't do it.Thanks everyone!

Every system you try will have flaws, or you may salivate over a feature that appears in other software.

I could help you with the basics if you decide to give them a try.