Back in the day, late 90’s my first purchase was a combo loan of an interest only ARM (interest rates were high then) at 80% LTV with a second loan loan for another 15% (I think this one was an ARM or fixed, don’t remember) and 5% cash down.  

Granted, it forced me to keep track of everything, which was cool, but it was tedious. 

At less fees and better breakeven/surrender value than Whole Life would force me to.2) Premium riders waived for disability. 

However, that won't work for several reasons:  1) The lender is not going to finance the $15k assignment fee2) The lender isn't going to consider the purchase price in this example to be $150k, they would typically use the $135k price in the original contract, and 3) In this particular example they may not even use the $135k price because it's not an arms-length transaction since it ultimately boils down to a deal between you and your father.I applaud you for trying to be creative, but ultimately what you're proposing isn't going to work and it's going to make the transaction a lot more complicated than it needs to be.

We seem to be returning to the “Drive until you qualify” days, where homebuyers are forced to move further out to find affordable housing.For someone who works in Marlborough and only commutes a couple of times a week, buying a multifamily home in Worcester might seem like a smart investment.

Areas that cash flow well (of course this is contingent on your down payment when financing the home) are states in the Midwest and Southeast of the country - reasonable purchase prices, great home appreciation, great rental appreciation and growing work forces!

That's not what's happening since costs are the driving force above all else. 

They don’t even need to force a BK.  

For instance, Choose Chicago (I used to work for them) is the marketing arm for the city and they drive huge pieces of business that will drive hundreds of people into downtown selling out all the hotels and driving prices crazy high.

If I were forced to pick, I’d lean towards purchasing two properties to diversify and spread the risk while potentially increasing your overall cash flow.