@Dan H.Safe to say you're a seasoned investor.

Any seasoned real estate investors out there with location tips?

He does this for mine for a low flat monthly fee and he really helps fill up the weekdays/off seasons and optimize booking revenue during the peak times.

DSCR requires No income, No Taxes and Commercial requires a PFS, occupancy ratios usually above (90%), Credit scores above 720+ much higher assets for (PITI reserves and overall risk, landlord seasoning, and more.A Heloc can be used in most cases for anything but when you are trying to buy a commercial building which is higher risk, the committee/UW can and in most cases will deny it if they feel you are over extended low assets or with no landlord experience, unless you have a meaty amount of equity to cross collateralize for a junior lien on another property.

For conventional loans via Fannie, I know that there is a 60 day seasoning for downpayment funds for conventional loan. 

The first floor is rented out to a seasonal business, they pay year round, $1000 a month.

On the other hand, the tenant may be more likely to move to a different apartment since there are more options on the market and they could find a better fit.I think you can make an argument that it's actually better to have leases expire in "slower" or less desirable moving seasons like the fall and winter.

Just got to shoot those bullets wisely, and play it conservatively but money should definitely be deployed I firmly believe. 

With the season in Sarasota County considered November - April, what is the best way to market the property as a Medium Term Rental (at least 30 days)? 

There is no requirement that the funds need to be seasoned.