A lot of full time teachers/engineers/parents/workers use PPC to grow their part-time REI hustle, because they have limited time during each day. 

I use it, though I hate it, but I avoid problems by setting criteria such as how much in advance a party has to book, minimum number of nights, requiring either a large deposit or purchase of insurance, house rules & photo id requirements prior to arrival, withholding check-in information until just before arrival and sending it to a verified cell phone number.

I hope you can make me smarter in this regard. this is not correct -- a person, or parents of a minor, have to apply for the Soc Security card number. 

My parents own a home in MD and owe about 500k on it.

We typically stay at my parent's house since they have the room for all of us.

I am a bartender and still live with my parents.

Treat homeowners who need to sell because they are in financial trouble like you would like someone to treat your parents.Unless you hate your parents, this will always guide you down the morally correct path. 

If you believe you have paid in enough to date through W-2 withholding and the expectation is that you will not owe considerably more that might be an option. 

I have never had to withhold a deposit except for one time.

Also note that he cannot withhold rent from you.