This is literally the entire reason these companies exists - to get this stuff right.As for why, I have no idea why there has been an uptick.

Reason why is because FDIC Bankers "Do Not" charge points on traditional programs like primary homes, standard investment purchase and refinance, Second home/vacation homes.Lenders, Brokers all charge points to meet their Loan officer compensation plan (commission).

Loan terms seem reasonable.

One thing I'll add to an off-market deal is you might find a seller willing to do seller financing.You said, "I don't think the time exchanged to manage SFH would be worth my time and the cash flow most likely wouldn't be reasonable enough to hire a property manager.

We are looking to buy a condo in Chicago as the new rental, for a variety of reasons, but most importantly because it would rent better in the city, and it fits our desired price point (so we can allow for the rest of $$ from the sale for paying off their Oregon home and pay all, or some of the taxes on the boot). 

Hi Jasmine-Congratulations on being ready to turn your primary residence into a rental.Your question is should you use a property manager or self-manage your property.If there is enough positive cashflow or you can afford to pay a property manager, I always recommend doing so for the following reasons:1.

Generally, the coverage of the policy will state; “The coverage of this policy shall continue in force as of Date of Policy in favor of an Insured after acquisition of the Title by an Insured or after conveyance by an Insured, but only so long as the Insured retains an estate or interest in the Land, or holds an obligation secured by a purchase money Mortgage given by a purchaser from the Insured, or only so long as the Insured shall have liability by reason of warranties in any transfer or conveyance of the Title.”

It seems like a reasonable approach, but as you say, we'll have to wait to see what the final version of the law (if it indeed becomes a law) looks like, then figure out if a European corporation with third country investors is a reasonable solution. 

By the way - for the same reason the 1st position lien holder will be uneasy with 100% CLTV, as a buyer I would be uneasy with it as well.

I got a reasonable discount on the purchase price, and it has made me a good amount of money over the years.