By systems I'm talking CRM: a way for you to manage your sales pipeline, moving new, organic leads from clickers to renters and past guests from one-time to recurring. 3.

Also, do you suggest we create a new bank account to manage property? 

Consider your comfort level with managing several mortgages and the risk of vacancies vs a slower but potentially more rewarding path to ownership.

The scenario you described is akin to playing the role of a lender and paying yourself the loan percentage—investors pay themselves much like how a bank or private hard money lending institution would handle it. 

Rent out whatever rooms you can in your primary residence and manage your roommates/tenants yourself.

You will pay them for their expertise, but with such a high price tag, I don't know that I would take the role of GC myself and hire my own subs. 

I just bought a building with my sister where we are 50/50 partners but I am managing as it is in my location.

Echoing more of the same - We manage 65+ units ranging from $80 a night to $2,000 a night we typically get negative reviews on a monthly if not weekly basis. 

Anyone have experience with Tripple E Reality or AMG Property Management?

All are operated by management company.I hope that makes sense!