As you mentioned cash flow can be a difficult pursuit especially in the early stages of ownership.

If so, what is your pursuit/desired outcome? 

(It sounds like) this is something you are doing on a regular basis for the pursuit of profit, you are actively engaged with other investors to loan to, while it isn't a full time business, you are in the business of loaning money.

Maybe he inherited the properties or maybe he is in hot pursuit of an early retirement, feel him out it may open a unique opportunity or be a dead end.

"The Pursuit Of Happiness" is one of the best.

That was at the time Quinnipiac University was growing rapidly and Hamden residents started renting out their homes to students.I wish you well with the rest of your studies and in the pursuit of a good house hack!

I will DM you my contact info if you want to tag along with me sometime.PS- I am also interested in starting a rookie-level mastermind type group locally, to help one another stay accountable to our goals and active in their pursuits. 

I'm Joe, a 27 yo pharmacy manager who is looking to get into rental properties to aid in my pursuit of generational wealth (...well that... and pharmacists salaries are projected to decrease year by year, dropping already from 55/hr to 46/hr in 1 year...).I grew up helping my dad with his rental properties, he self-managed them all and I loved spending weekends learning new things with him and my other brothers and sisters.

If you are in the Multi-Family game either passively or actively, I would love to connect and see how we may be able to help each other continue to grow.Good luck on the continuing pursuit of your goals. 

I much more identify with the pursuit of financial freedom and increased time to spend with family, which are values that I have seen embodied by every real estate investor I have ever met.I look forward to being a resource as much as possible to this community!