Everyone has a unique combination of skills and circumstances. 

We have a unique property we are looking at in upstate NY.  

Muskoka is a very unique market in it's own.

This step ensures compliance with local regulations.From my experience, when I had an STR in Cleveland, I only did the regular rental registration, so make sure you complete both registrations to avoid any issues.Cleveland is a popular spot for STRs, especially for visitors coming for sporting events and medical purposes.

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

Definitely a unique position to be in. 

If it's just speculation, start by reviewing the law to see if there are any unique requirements for a business.

Your record of this deposit (via teller slip or online transfer) will be your receipt of payment.This elimates complextity and the additional steps/rules that come with using a third party to collect rent.I get an email alert when a tenant makes a deposit, and each rent amount is unique so I know who has paid in case they don't have the teller add a memo to the payment.They can transfer funds online, or walk in to a local branch with cash, personal check, wampum, etc. 

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

Make your furnished unit unique and market it everywhere.