Personally I love what you are capable of doing I am just not very good at it so I outsource to individuals likes yourself with right set of skills.What type of investing are you most interested in? 

You would have to evaluate each deal individually and compare each one to the S&P.

Since they can't do each property individually, they use comparable sales to make broad generalizations to determine percent changes.

I understand tax advice is specific to individuals/timing/location/situation and I need to hire a CPA -  but in general how would this be done?

What's going on with the individual line item operating expenses? 

In the future, if you have a partnership, both individuals must agree on all points.

Ask to see the track record of the individuals involved in any "guru" programs.

A private lender is typically not a business, its typically an individual.

Neither interfaces or reports seem great from the landlord side and since I would like to start creating more separation between the personal/rental/individual property finances I figured I could benefit from Baselane or Stessa through their competitive interest rates, low/no fees, and property management software. 

Right now, there is a very popular individual on Youtube and Facebook, and apparently appears at Bigger Pockets events, who published his book, that advocates these techniques  for buying for full price off of the MLS and borrowing closing costs.