If you go the 2nd route you need to be in control of the statement delivery (monthly statement needs to come to you) so you can be assured the mortgage company is actually receiving the payment.

I assure you it is not as interesting as the investor side but an essential part of getting a real estate deal done.  

Some banks are more religious about their price drop schedules than others, but I can assure you none of them are taking offers at 80% of whatever they believe is market value at that point in time.Assuming you are in a seller's market, your chances of having a below market offer accepted on a listed property might be somewhere between 1 in 50 and 1 in 100.

I am hoping the ~$160,000 in combined W2 income (and no other debt) will provide lenders with the assurance they need to take less than 20% down...I have a friend in a similar financial position as us (although he makes the $160,000 and maybe more on his own) who managed to get an 80 (2.9%) - 10 (~5%) - 10 (down) on a condo in Boston's North End.Thanks everyone for your responses!

The owner has the deed, what's the easiest way to transfer over the deed while assuring everything goes smoothly?

Credit cards will almost assuredly get paid down to at least below 30% utilization.

A small job like that, most "reputable" contractor could carry the cost and bill you once until the end, but what assures the contractor from not being paid by a client?

Though it stinks, it's also your assurance that you won't get your STR voted off the island by the locals, as it's in a specific STR zoning.

If you are fearful of them tearing your house up by terminating their lease, and they leave the house in shambles in retalitation then I assure you without any question that these are not as good of friends to you, as your are to them.terminate the lease, they can be grateful for the subsidy you have provided thus far or not, but you should not pay a renter to do what they are supposed to do.

If there can't be an extension, should I pay the premium and hope we can still close, or let it cancel and get different coverage when closing is assured?