If you do call them best case scenario you get the listing, sell their home and end up with some additional buyer clients that did not end up buying this particular house.

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.

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

When in Due Diligence have a thorough inspection and get estimates for any work that is needed now and potentially in the next 3-5 years. don't forget about the tax benefits to doing the work upfront.

Although he is a banker, he thinks having the ability to operate as a broker and place loans with 30+ other lenders, in addition to his bank, is the "best setup."

It could go higher with additional work to the house.

If the stock market were real estate, you'd pay for 5 shares of Apple stock and get an additional 95 shares.

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.

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

I know hosts have included additional cleaning fees for violations as a deterrent.If none of these solutions work, you could look into completely independent HVAC systems for the two units, though that would be a bigger upfront investment.