To pick a location, I understand I want to evaluate median income, a large population of those approaching retirement age, and a decently dense population.

They did successfully place and a tenant who even pays early, which is a very nice change.

Since most properties on the market here have inspections and a disclosure packet up front, it will be difficult to get those documents without MLS access. 

Quote from @Jaycee Greene: If you go the conventional/DSCR route, these are considered "Commercial" loans and the properties are referred to as "Non Owner-Occupied" and, as such, the cash flow of the property is most important, and your DTI is not generally included in the underwriting.

It took about a year and a half to stabilize the property but the property is stabilized and cash flowing.

Purchase price: $480,000 Cash invested: $75,000 Purchased as a single family home with a basement and a seperate entrence.

If your partner is a contractor and wants to keep busy, that could be a different story, but I at least consider looking at long term ownership plans and flipping as very different businesses and a lot to learn on both, so not sure I'd risk losing money and time dealing with flips. 

And as for a multi, I'd argue it's best to build, not buy, especially if going out to the NW "burbs".

I have a 1/1 and a 2/1 and although I'm seeing lots of different types of travelers, the ones who have been booking my place have all been traveling medical professionals.

And if there was any land available, it'd cost an arm and a leg.