Meaning the grass is not cut and nice looking, its a smaller older hasn't been updated gas station, its combined with an 18 wheeler parking lot. 

Mostly all older equipment at least 15 years old.

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.

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

Purchase price: $38,000 Cash invested: $48,000 Single family, Home in an older established neighborhood needing complete updating.

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)? 

Not knowing the exact age of the trailer there is secondary financing out there for buyers of land and older mobiles that have been moved previously- but it is usually more expensive. 

Long-Term Maintenance: Older homes may require more repairs.

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

If developers do not build additional housing units it is likely we will see rents increase on much older and likely inferior housing compared to what developers would have built.Major Housing Developer Pulls Out Of California