Kevin,  I tried working my sign company and lending, it is a lot. 

I was going through the posts in bigger pockets and try to find a good company to do Cost Segregation.

i.e. what don't I know about managing a property management company that should give me pause about this?

Hey Ryan,Congrats on the success on your first invesment! 

Quickbooks allows for you to add multiple debit & credit cards/bank accounts associated with a company.

It would be helpful to understand the seasonality and other factors that affect bookings.Also, how long have you been a host, and what have you found to be key to your success?

Do you need a title company for a deal you've already made on a small 2-4 unit multifamily?

Someone like SunBelt, but there may be dozens like this company who regularly sell such businesses, works with consultants who have buyers looking for these businesses, and have experience with valuations.Does the business own the real estate or do they lease?

Have you considered either studying property management or hiring an experienced property management company?

It is extremely common for PM companies to accommodate for external contractors - as mentioned above, it is your property at the end of the day.