Pick up the phone or stop by local code enforcement offices to make sure that you have a crystal clear understanding of local laws and regulations.

The withholding can also be stopped altogether, and only actual taxes owed will be collected by filing form MW506NRS at least 21 days prior to settlement and filing it with the Comptroller of Marylands office to get the exact actual tax owed calculated. 

Meaning if the borrower stops making their payments the investor can lose all of their investment.

All the various consumer laws exist specifically to stop bad actors from doing stuff like this. 

Stop jumping every time he asks for something.

So many hosts waste their prime real estate with Airbnb (the listing title) on generic adjectives and throwaway opinions. If you want more clicks, get straight to the features that matter most to your guests. That mea...

When a tenant violates even one term of the lease, you need to immediately send him a Notice To Quit which informs him of the violation and gives a cure period (set by state law) for him to stop/make it right/get in compliance - or eviction will begin. 

The area has certain advantages like shelter from regulation risk (pretty much as low as anywhere in the country if you buy in the approved STR tourist zones) and long term security (people aren't going to stop going to Orlando anytime soon). 

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

You mentioned various places to put your money.What is your expected return along with level of difficulty for each venture?