Pros and Cons of Month to Month lease vs. Long Term leases

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What % of you all only do month to month leases and why? 

Here's my situation below. 

I have a tenant who's trying to build credit. He's not the best, but we value his cash flow. 

I'm considering renewing his lease on a month to month term versus having him sign a long-term lease. The lease I inherited didn't capture a security deposit and there wasn't a pre-lease end penalty. 

I'm dropping by tomorrow to do an inspection and depending on the condition of the home I may consider a month to month lease w/ minimal security deposit

Here is my rational

Pros - 

• Canceling the lease would be easier for me if he is on a month to month
• He feels he has more flexibility.

Cons

• If he was on a long-term lease, there could be some recourse if he vacates early.  But it would the classic squeezing "blood from a turnip" scenario