In the beginning the goal would be to get into the market so you could start taking advantage of appreciation, tax advantages, and debt paydown. 

Additionally, I was not making enough from my corporate job to support any kind of significant mortgage payment.

Thanks for any additional input you have time to put forth. 

That would be a helpful addition to your plan as you would further reduce your cost of living.Also don’t forget from that $600 you are planning on getting in cash flow you have taxes, insurance, maintenance, capex, and vacancy to consider.With two homes, you may want to keep that extra $20k as an emergency fund rather than spending it on a third property and then be left with no emergency funds.

Cash-flow is for "keeping the lights on" as in covering operational expenses to defend against any need for additional capital investment. 

Some carriers won't allow insured to be a trust, so in that case do it in your company name with trust as additional insured.

So you have some great resources right off the bat, my additional Referrals would be too many :)

So he needs to be more ITM than  the 1.25:1 ratio.With that said, to answer the question-- figure out your debt or income.

We already paid them a pretty sizeable entry fee ($30k) to cover some of their equity and debt in another project.

An umbrella policy for additional liability.