Local presence: location that you can access directly and self manage - unless you want to leave 20-25% of the bookings for property managers that might (or not) be reliable3. 

Conventional loans have minimum standards for condos and the presence of an HOA is one of them, you also must have a budget, and at least 10% of that budget must be held in reserves by the HOA. 

They are most likely to help you out with creative financing as the presence of checking and savings accounts allows them to have enough coffers to maintain loans on their books (called portfolio loans).

Eventually, we want our presence in the marketplace to be as such that people know to bring us opportunities. 

Since this is all new territory, it would be good to know where to find a company (perhaps smaller group to absorb the mentorship experience) that is willing to train.For reference, we are in the Metro Detroit area.All suggestions are appreciated!

There isn't much of a VRBO presence here but theres a few chain hotels and many new apartments going in. 

Seems like right now in my areas right now: Westchester County NY, New Haven County CT are just true shark territory and IM not a shark.....

small towns are very hard to lease out if you don't physical presence.

I know this is crossing the commercial territory but I would be interested to know the strategy there.

@Isaiah FranklinIt would depend on your goals and views on what is a "short-term rental" but I noticed you're from Cincinnati which has a strong healthcare presence/industry.