Or perhaps it all depends what kind of entity we are operating under (S corp, LLC etc).

Quick analysis is derived by taking annual Gross potential rent, subtracting an appropriate expense ratio (a percentage of income that is typically used for normal operating expenses+reserves+taxes etc.) and dividing by a market Cap rate.

@Scott ShopeI operate a property management company in Indianapolis called Intrigue Indy.

When you owner operate you run the risk of doing an action that may make you personally liable even if you have an LLC. 

Hey @Taylor Smith,There are a lot of factors that play into the decision, so I would always start discussing what your current portfolio looks like, your future goals, what states you operate from generally along with a multitude of other questions.

*MOST* of the time, unless you have something that's a maintenance or operations nightmare (i.e. you're driving a 10 MPG Hummer), the cheapest thing you can do with cars is keep the ones you have until the wheels fall off.

This was a really good reminder that we need to put together some sort of operating agreement and some other policy paperwork as well but I'm not sure where the best place is to start or should we just get a lawyer?

The broker was initially trying to close the business portion first by 1/15/19 (which I think is why my father in law agreed to the transition date of 1/1/19) where the ABC license would close later and the new owner would just operate under a temporary permit or something along those lines.

All great advice.Follow up question... do you prefer to work with one-man operations or companies and why?

Small operation the Property Manager will know you as well as all of your tenants personally.There is a trade off though.A big company is a proven entity whit proven policies & processes.