Long-Term Rental Rules: Even though my properties are long-term rentals, are there any tax benefits I might be missing if I occasionally rent them short-term?

Asking in the correct forum will get a better response.Read the RULES!

Depending on where exactly the property is located they may have some different rules/laws in place.

The FCC rules are here: https://www.fcc.gov/sites/defa... 

If the rules are violated and you were lazy-fare in addressing the violations, YOU become directly responsible legal and otherwise.  

Owner occuppied loans regualted in every state .. must have state license and NMLS registration.NON owner occ loans on 1 to 4 units are regulated same way in about 15 statesin the other states they are unregulated.Keep in mind though investor loans do not follow the same rules as owner occ and rates can change charges can change closing dates can be blown through etc

Until the conditional use permit is applied for, an operator of a short-term rental is required to apply for a short-term rental permit.

In this economic environment, creativity rules. 

Plus now they are trying to pass the buck with regards to the the STAR rebate we get here in NY state (if eligible and applied for).

If you want to connect buyers and sellers together get a license.New York has the most stringent rules for real estate.