It's doable for sure, but I'd suggest having a PM initially.

If anyone could share some of their experiences, particularly on how they went about initially approaching the occupants I would greatly appreciate it!

I have an initial list of currently available properties clustered in specific areas, mostly Massachusetts, that are turn key and cash flow positive, minus some development, consisting of $260mil worth of real estate.  

A hypothetical to see how people factor costs when rolling equity forward into additional purchases.For this example assume  you purchased property “A” for 100k, and put 25% down. 2 years later you sell it for 125k so you now have 50k (25k from your initial down payment + 25k in equity).

@Adaze Foltz  Benefits:Direct to the source; more control over the receipt of the funds (initial and any rehab draws); able to not just establish a relationship, but also perhaps gain referrals of other private lending sources (those that are happy with the returns and payoffs - talk (boast) to their friends); faster to the table; can negotiate the terms (rate, when payments are made, other fees and when they are paid, etc.); usually nothing reported to credit bureaus.Risks:Using up the private sources money (tapping them out); The private lender didn't receive their payoffs on other loans as anticipated so they are short of funding your deal(s). 

Initially, he sent me a friend request via LinkedIn and then we connected.

Their initial plan was to do flips.

I knew exactly what I was doing using my initials. 

@Andrew Postell If the initial mortgage (LLC to individual) is for ~75% ARV, but initial purchase price is for much less than that, then how do I make the proper paper trail for the lender to see? 

The city has a relatively low cost of entry for real estate, which is beneficial if you’re looking to maximize your investment while keeping initial expenses manageable.