I'm thinking of managing myself and looking for a fee based advisor who is versed in tax/management.

I am based in Greater Philadelphia region and worked on a deal the owner sold 75K sq ft self storage and kept 20K sq ft of contractor specific self storage.

I own a Vacation Rental Management company based in Branson.

After visiting the property, I decided not to offer based on what seemed to be many interior issues, a roof that’s seen better days, and more tenants living in the unit I was allowed to view than I was expecting for a 800 square foot space. 

You'll want to cover your bases legally and financially.

if cashflow is the goal, then a) choose a market to invest in that's cashflow-heavy, first and foremost. note: living in a property for a year doesn't necessarily build equity. your principle paydown year 1 ain't much & if the market dips a bit, you could have no or negative equity at the end of y1. just something to consider.note: appreciation in general is speculation. we can make educated guesses on what's going to happen, based on what HAS happened, but this isn't the 'perk of RE investing' to focus on when you know your goal is cashflow. ignore appreciation for now.if the goal is cashflow, why not just start with a rental?

Based on the terms of the lease, the company took out a commercial rental insurance policy for their time while there. 

Sounds silly, but base level service is assume tax filing and compliance.

That would be a big dictator of your closing costs as several of the factors are based upon closed price.

I sell insurance and am commission based so I would like some sort of passive income.