Do you need to supplement active income with more passive income?  

If the property doesn't fit the rule, I'll use MPP to aim for a target profit.

Our main criteria are:- 75% market value- Cash flows even with a 100% LTV 8% interest only loan on it (aiming for $100/month at least)- Decent area (doesn't need to be great, but not a warzone)

Of course I don't assign I close everything I aim at value add then resell. 

Personally, I aim for cash flow but occasionally do flips for cash.

If you needed to move for work (or another reason), you could live in it for less than 12-months.In our programme here in Canada, you can have only one insured mortgage at a time (legally) ... check out the details of FHA or other programmes available to you.Most such programmes are aimed at owner occupants and that is how the rules are structured.

We'd aim to rent it out, either short-term or on an annual basis, for the next ten years or so and then spend winters down there.Does anyone know a great Realtor in the area who could speak to short-term versus annual rentals in that market?

If you believe late fees, which are  for the purpose of training tenants to pay on time,  are supplementing your income it is obvious which of us is operating a mom and pop hobby investment.

In addition to the obvious costs, we don't know how independent any of our kids will ever be, and we need to be prepared to provide for our kids for life - meaning I have Supplemental Special Needs Trusts to fund for each of the kids. 

I'm looking to supplement my income and build wealth by buying a multi-family property that I will owner occupy starting June 2018.