I normally do a lease for the first year of the tenants occupancy.  Thereafter, it's month-to-month.  I'm reconsidering this method for several of my properties.  

If I haven't renewed a lease for a tenant beyond the first year, and they are now there 2+ years, would it be out of the ordinary to issue a new one now?  Why I am thinking about this now?  More so to avoid a tenant leaving in the late Fall/Winter months, when it's more difficult to find a tenant.

Actually, here in the NYC area, a lease has almost become a worthless document.  If a tenant wants to break a lease, the landlord has to prove that a new tenant has been diligently pursued at the same or higher rent before legal action can be taken against the existing tenant.  Also, new legislation is on the table which would make leases automatically renewable for the tenant.  Not sure if I just answered my own question.  However, I'd like to think that a good tenant who signs a lease will abide by it!

Interested in feedback!