B) are you comfortable with the collateral (real estate) that the Note is secured by.

If it is his money and he is not comfortable investing it before grad school then he should not invest.  

My philosophy is if I want to try a different style of REI such as wholesaling or flipping I can always try it later on after I have focus on my buy and hold properties and am bringing in cash flow that I am comfortable with.

Lease to own vs land contract scared me but I feel more comfortable now.

I have also been looking into " freedom mentor" as I would feel more comfortable with a mentor, but willing to take help from anyone in the game. 

I lend to them when they need it (if I have the cash available and I am comfortable with the deal) and they lend to me when I need it (if they have the cash available and are comfortable with the deal). 

Its an 1 - 1 1/2 away but apparently a lot of the rock stars feel comfortable enough to invest out of state.   

Also, if you network with other local investors, they almost always have cash they would like to use to be an equity partner in a deal, especially if you use workers that they are comfortable with. 

I would address that with them just for your comfort on a daily basis.  

If I am going to expect my PM and/or send my own maintenance guys out there, the neighborhood needs to be comfortable to be around in.