Definitely tougher to get tenants in the winter months. 

I did this for one of properties in a tougher neighborhood and it worked out great.

Sometimes it helps for the tenant to think in terms of - oh God, do I want a different landlord who might be tougher on me? 

I have done a similar variation on this strategy though (see below)A few more ideas...Cons: Tenants who already have plenty of furniture (and then some) may be turned off; Turn overs can be tougher with more items to clean, inspect, track, or move (work around) for painting, cleaning, etc.

I guess my biggest concern would be dealing with a vacancy during the tougher winter months (if they were MTM) or even 6 months would bring them into February.

But, definitely don't give him any deposit money, until the place is empty and clean and he hands you the keys, and then, while you are waving goodbye, change the lock before he can come back.It would make your life easier if you had tougher tenant criteria the next time around. 

There’s way more cash flow to be had In those Tougher areas .

If I was a seller it would be tougher to take the opinion of a buyer’s general contractor :)

I suggest growing a tougher skin. 

Hard Money is easy to find, private lenders are a bit tougher.