I understand the importance of finding the right lender experienced with first-time investors/buyers and supportive of your unique positions as a business owner and W2 employee.As an investor, my network includes trusted mortgage brokers and lenders experienced in working with first-time investors and understanding the nuances of investment property financing.

I'd suggest you understand the differences between lending and equity positions and follow the tried and true methods of partnerships, joint ventures etc.

We all take our lumps when we are new but I am hoping to help some other new folks on both sides of the fence understand how to best interact2.

I benefit from their ignorance (my rents will increase ~$50k this year), but would prefer that they had a better understanding of consequences.  

Might be worthwhile to understand what you'll be asking of a PM (which you already seem to have a handle on) before you hire them. 

I do #2 and #3 as they apply with a preference for rewiring.This exercise is helpful in developing an understanding of which circuit breakers control what.

How do you go about accurately generating an annualized return % in this situation (I understand IRR is the superior calculation but investors like to know metrics such as equity multiple, annualized return, and IRR)?

Rather than pay off your debts, you could take your initial seed money to invest with a rate of return.The big thing right now is just understanding and ensuring your rate of return on any investment you do with the cash on hand is higher than the interest rate of what you are paying off.

I do plan on keeping this long term and my understanding is I can always refi it into another loan.

Marlborough I understand, is really looking to add more units and have the city truly prosper so I believe you could achieve this.