Prefer to cashflow as close to day #1 as possible.No problem!

Personally I'd prefer a single family over a condo just because of the control aspect and HOA nuisance. 

I recommend you consult with a lender with expertise in investing, preferably someone local to you, to discuss the lending options best suited for your goals, strategy, and tactics.

The question is what niches will support the MTR paradigm.

You learn the most about being an agent in the field and by choosing a good first brokerage with good training either in-person or online, depending on your preference.

I'd prefer to play it as safe as possible.

One form of that is finding a specific niche subject matter expertise...something like an ice fishing cabin that those of us who don't know a thing about the category would never think of investing in.

Become THE EXPERT in a niche - the GO TO person2.

I definitely prefer to be an asset and not the kind of small business person that doesn't enrich or contribute. 

I definitely prefer this option as the whole point is to get built-in equity.