But back to my first point, if you can use the "tax benefits" at all, if so how much, and how they effect taxes owed at the back end of the deal are all unique to each person's situation.As for refinances, some syndicators model refi's and other's don't.  

Though it sounds straightforward to hire a PM and get the property rented, for some reason it gives me cold feet.

Question one is, does this sound like an inherently bad idea to anyone?

Sounds like a stinker property, and an ambitious plan on behalf of the buyer, I'd just sell it and be done with it if you're burnt out.

But what Ken COMPLETELY misses is the reality and fact of EFFICENCY, what actions/output EFFECTIVELY and EFFICENTLY will lead to off-market-deals....... 

The easement must be evidenced by written instrument recorded in the office of the clerk of the circuit court in the county where such land is located before the recording of such tax deed or master’s deed, or, if not recorded, an easement for a public service purpose must be evidenced by wires, poles, or other visible occupation, an easement for drainage must be evidenced by a waterway, water bed, or other visible occupation, and an easement for the purpose of ingress and egress must be evidenced by a road or other visible occupation to be entitled to the benefit of this section; however, this shall apply only to tax deeds issued after the effective date of this act.197.573 Survival of restrictions and covenants after tax sale.—(1) When a deed or other recorded instrument in the chain of title contains restrictions and covenants running with the land, as hereinafter defined and limited, the restrictions and covenants shall survive and be enforceable after the issuance of a tax deed or master’s deed, or a clerk’s certificate of title upon foreclosure of a tax deed, tax certificate, or tax lien, to the same extent that it would be enforceable against a voluntary grantee of the owner of the title immediately before the delivery of the tax deed, master’s deed, or clerk’s certificate of title.

I’m having a hard time finding information on the financing piece of how house hackers build their real estate portfolio – is this plan generally sound?

The other home sounds like more of a set and forget type - move in and then get back to living your life as you see fit. 

This gives additional reassurance that this specific 'fringe' region between Waldo and Marlborough is a sound area to invest IMO. particularly in the long term.Main issue with the Quads is price: they started at $550 asking in September of last year.

I am curious though, if these deals are as sweet as they sound...I’m also curious to hear about the complications of owning/investing overseas?