Yes, long-term rental clients sometimes don't want short-term rental next door to them, but you are the owner and landlord and set those expectations up front so it's on the table before they lease.

You might have other options to explore to drum up liquidity (HELOC, Margin Loan, Policy Loan, etc) that can supplement your HYSA in the DP.

If the rents are already nearing market rates, will she be able to go up that much? 

Its how come I am so entrenched in funding in the mid west till this day.. 

I've come across some interesting niche strategies like buying small plots of land and slowly building, investing with a team/syndicatikn (if you find a good one), or even funding smaller infrastructure projects for commercial properties (e.g., electrical, plumbing, etc.). 

So if I do a good analysis of the property (including all the costs) and the property generates monthly CF with a DSCR above 1.1, I would be removing a big risk because the numbers add up.

HELP :) can you split the lot?

It’s hard to really get good at it without doing a lot of deals because the licensing course doesn’t teach you much about actually being an agent, that comes from doing lots of deals and learning by doing it every day.

It takes a lot of time to build up a reputation in the wedding/event space.

I have a bit of a soft spot for the area as a UF grad, and I still come back to the area every year or two.