That's a good idea.  

Does anyone have any idea what this would do to resale value of the home - owning the actual property outright as opposed to owning the building and ground renting?

Still not a bad idea for buy and hold.

I was born and raised in southern CT and I think I have a good idea of what's what in the area and hope that will be an asset to me in local real estate.I currently work 9-5 as an engineer at a small design and consulting firm and I'm looking to enter into the real estate market on the side (for now!).

Owner occupied loans are a little more tricky with our system but me or a team member would be happy to bounce ideas around with you.

I think house hacking your first property is great idea!!!

I would run comps in the area to get an idea of his property is worth.

Is it a good idea for me to mortgage another 500k?

So what I am saying is, it is a bad idea to play "chicken" with the IRS in hopes of gaining a leg up on other bidders at auction.  

Here are some idea: if the person that wants to invest can pull equity out of their home and use that, might be able to get a loan in that country with a sizable down payment.