The next problem we are having is just trying to get ahold of him, he's a shady character who we are sure is a drug user of some sort and makes his living by stealing.

As a former FL narcotics detective, having a lot of drug activity without violence can still be bad for your business.

Having all of my application material online helps weed out the Luddites, drug dealers, conspiracy theorists, and other "cash only" type mentalities. 

I'd rather miss out on that $100 and not have to deal with the FBI over an alleged drug ring scandal, nor (which would likely be more common), haggle with the tenant over $5 that exceeded his $200 utility spending limit.You could say "$5 isn't worth arguing over", but understand that once you set expectations, you need to enforce them consistently or people in general will take advantage.It's really up to you though.

I have a budget spreadsheet that I update each year based on previous year averages, and every year different issues pop up that cause me to spend my profits making the expenses instead.The first year I was the landlord at 22 and people didn't take me seriously, so I got taken advantage of by listening to every non paying tenant issue (flat tires, grandmas sick, have to water the dog, etc. ) The second year I had a property manager who was both stealing from me and renting to drug dealers.

Hello, Well,  having lived in a recovery drug and alcohol safe home.

Also, being a drug dealer, I was concerned for my family's safety if things got ugly.

The students use drugs and their dealer carries a gun and it went from coke to crack to whatever they use to kill themselves these days.

The important thing to me is that this isn't from drug money or something like that.

I have yet to have a stripper apply that didn't have a lengthy arrest record (generally drugs and prostitution) that disqualified her long before her source of income was considered.