My wife is an accountant for a large city out here, in Orange County.

Again, very sorry you had this happen but we've all been through it before.For the most part, large banks are out for us as investors. 

At 0% you will take a very large discount.   

I love the area but as others have mentioned its really hard to get cash flow unless you are putting 25-30% down which is a large undertaking in Boston.

His warnings were largely unheeded. 

To me the quadplex would be dual purpose, while you are not living there it serves as a reliable stream of income, once you move there, you could live in 1 of the units while you build your permanent home, and you could also use it for when your family comes over for large gatherings.A 2nd option might be to build an RV park, Unless their are zoning restrictions, you should be able to build one fairly inexpensive, with a septic system and either public water or a well, you can keep your costs to a minimum by doing gravel roads, which are easier to remove later if you don't want them. 

Especially HOAs and $1100/month is a large chunk to have to compensate for in a rental.

The details and logistics very much depends on what you are trying to build and how large.  

I am planning to do more buy and hold, but in little medium to large scale.

Now how far will this fall, or how deep, too many variables but you'll see little mini bubble like formations come first then the air gets let out of the balloon.Your sentiment was right Collin just too, too early.