Recommend one of those markets being close to you, that you are most familiar with, and then 1-2 others that are easily drivable, and if you are comfortable with out of state/area then look at 3 or so that fit your criteria.

Were you comfortable doing a BRRR that could potentially mean a longer term partnership without knowing how you would work together?

That sweep account lets every dollar we have work for us, while maximizing flexibility.

I like the location so I may take my shot on an offer that isn’t as-is at numbers I’m comfortable with and if I don’t get the deal, life goes on.

One month bank account has been shared but that I don't feel comfortable renting to him/her just on the basis of that.

If you are in a more expensive market, will be working these deals full-time, have experience managing rehabs, etc then you very well may wish to use financing and maximize the use of your available money. 

.- You want to increase taxable income to maximize income in the DTI equation.

The way he views people and their issues is quite...desensitized.I'm looking for any words of wisdom on how to evolve mentally to where I am comfortable doing whats right for my business without losing sleep at night. 

There are even some property management companies here in Denver that specialize in helping investors who want to rent by the room to maximize returns. 

I'm not comfortable with posting a link to the calculator I used, but I just googled "cap rate calculator."