Discussions

My friend was renting out a room in his house for a few months. There was nothing on paper but he was being paid $500 a month. There ended up being some issues and my friend kicked out the renter but the guy still owed him $500 from July.  
Would it hold up in small claims court? Is it worth taking to small claims? Or is my friend out of luck since nothing was on paper?  
I realize talking to a lawyer would be beneficial but that costs a lot more money than he's got right now.

Without a paper trail it would be pretty hard to prove in court. Not only that though but if your friend wasn’t claiming this as income his renter could be a major jerk and turn the screws on him. Might not be worth his effort for 500 bucks!

Cut the losses, without any paperwork im sure its undeclared income in which case is a form of fraud to the CRA and a judge would most likely toss it out, but inform CRA which in turn could cause more problems for your friend

Why whenever you are renting especially like that get the rent for a month advance. If someone moves in August 1st tell them rent is do in advance on the 1st of every month so before they even move in first months rent is due. And even charge them a damage deposit of half a months rent then you can at least cover the expenses of the guy li Jong there hydro water etc

Charge ahead of time. A landlord can only charge a damage deposit half of first month's rent and the first month's rent in Manitoba. Anything above that is against the rental board and the tennant could fight it and win.  
 
OP you might want to ask the Manitoba rental board on what steps you can take. I am going to assume you are claiming the rental money on your taxes.  
The rental board can at least point you in the right direction on what steps to take next at the very least.

I know someone who is being taken to court by a landlord of a place they were living but wasn't actually on the lease agreement. Due to unforeseen circumstance my friend up and moved out after being there for 2 months and now the landlord is coming after her for a bunch of stuff. My friend didn't even do anything wrong, just packed up and left. Again she wasn't even on the lease there, her friend was.  
 
So landlords may have some rights in those situations it's up to the courts to decide on the end

What I said first months rent and half for damage deposit. But I don't know the laws however I do know that is considered room and board which has different rules.

rdp said "What I said first months rent and half for damage deposit. But I don't know the laws however I do know that is considered room and board which has different rules. "

Your first post was confusing I thought you meant pay a month in advance. You said advance....

Well it kind of is in advance though you pay for the month then stay the month then pay the next month then stay the next month instead of stay a month then pay then stay another month then pay. Because that's the only way I can think the OP would be out the money.