I own one rental currently and am looking for more.

I've actually seen this happen and it's ugly).

James Wise called you out on ties/ownership in this PM entity, and you played word-salad games trying to pretend had no connections to it. 

Purchase price: $150,000 Cash invested: $100,000 I have rented this for 4 years now I am renovating it for an Airbnb now once on airbnb it will do 10-20K a month What made you interested in investing in this type of deal?

Lived in the upstairs unit for 3 years until I got married and bought a house What made you interested in investing in this type of deal?

Tenants that ask for these types of things are typically entitled and will take further advantage in the future if you do not curb this behavior.

This will give you extra cash flow in the first year and/or the early years to maximize your tax benefits and make your dream come true.

If looking to scale flips and create systems around it to minimize your time and involvement, I'd highly recommend putting a team in place that can handle the day to day operations. 

This might turn out to be a good approach.   

This has not worked more then it has worked.