I totally agree with you on the HOA's, it's definitely one of our main concerns!

Offer is $605kOffer 2: Some unknown agent using Bank of America, offer $610k.Listing agent explain hey, they offer may be slightly lower, but A, I know Bank of America is going to cause a bunch of headaches in this transaction, and if the buyers agent who has no track record is letting a client use them, they probably dont have a clue themselves. 

I have recently become financially conscious after getting myself out of a mental stalemate caused by what felt like unmanageable student debt.

To think that you alone can take on all of the opportunities that are present is a little far fetched imo haha but I can understand the concern.

No issue at all with just buying a multi (or any property) as purely an investment.Perhaps you're concerned with down payments. 

My only concerns is what if my residential rentals appreciate more from recent sale comps?

If I were to pull out 80% of what its worth, it causes my ROI to go up, but brings my cash flow down.

From what I can tell, their biggest concern will probably be “how are you going to service the debt, i.e. make the ongoing payments on a monthly basis?

My concern is someone familiar with the territory might just give me a guesstimate based on when the property last traded Plus or minus any appreciation.

I am concerned that it appears you are considering renting to someone you have known many years.