You should only have to change when your current software has a flaw or lacking feature causing you to spend too much work on a work-around.

Be prepared to spend a lot of money creating the infrastructure.  

Read "Long-Distance Real Estate Investing" by David Greene, then spend some time reading through the forums.

Framing your position as fair such as explaining the difficulty of finding renters during off-peak months - might help maintain a positive relationship and reduce risks of property damage.Prepare for What’s NextEven if the tenant moves out early, ensure you’re protected.

A combination of extremely tough long term tenant protections and the economics of short term renting being a lot more attractive. 

I 100% know that he's going to spend a decent part of the 2 days trying to get me to invest in Cardone Capitol.

thanks. you will spend more time trying to figure out whether or not its required than actually completing the form. it takes five minutes. 

Trust.I am spending upwards of $7K having my STR to LTR back to STR repainted and refurnished.  

The tenants should have renter's insurance to protect you.

Work with a real estate attorney to draft a formal agreement that outlines responsibilities and protects both parties.