My concern is not being able to find quality tenants that can afford the rents I’m looking for to be able to live for free.

A lot of positive stories but moving from A to mid-west D is concerning.

If the fourplex itself is a good deal is the underfunded HOA something to be overly concerned about?

Leave it to the tenant.What do you guys do for your out of state properties? 

Hi, I did private lending to one of my friend , he mortgaged his investment property as first lien with me.agreement was that he will pay interest monthly, and he was almost regular on that.in July that property got deadly fire, in August beginning he paid my interest for July and didn't mention anything about fire.today, he called me and told that he wants of pay off(but he didn't pay last month's interest).I said OK start processing for payoff, but pay me last month's interest asap, then he told me that house went on fire and he is hoping to get insurance money and then he will pay, he has no money to pay interest .Now, my concern is should I wait and watch or I need to take some pre-action to make sure that I get insurance money since I am on first lien.

@Brian Erickson if you're looking into markets with landlord-friendly laws I'd be most concerned about the purchase.

My biggest concern is the time of year this eviction came around. it will may be difficult to find a renter now 

I will specialize in condos and have specific zip codes for my market/territories.My main concern is rehab and management of condos.

Well maybe not so fast.While it does not make sense to me, I provide for your reading enjoyment the following links /  Court Case;https://www.gpo.gov/fdsys/pkg/USCOURTS-ohnd-1_08-c...andhttps://www.casemine.com/judgement/us/5914fbf2add7...This property was recently listed and so I was doing some research, ran across the case and learned a thing or three.The synopsis is (not a lawyer so maybe I haven't read it correctly) and leaving a side the fraud of one party (which he eventually was found guilty of), the eventual purchaser, purchased in good faith and was declared the 'owner' with good title.

If you are worried that you will not qualify for more investments after you buy a primary residence because you have no rental income offsetting the monthly debt service, that is a valid concern.