Tenant Wants to Move In Before Lease Start Date

[Mark Campbell]

Hello, everyone I am a new landlord and encountering my first issue.  Soon I'll be moving out of the first house I purchased and I'm converting it to a rental property.  I signed a lease with a tenant and they will move in several days after I move out.  The lease start date is October 1 (a Sunday) and I cancelled all my utilities on September 29th (Friday) since it has to be on a weekday.  

The tenant signed up all utilities to start September 29th and now wants to move in on that day.  I initially told him no the lease starts on October 1.  He contends that he is a great tenant (his background verifies that) and he is paying utilities that day so he thought he could move in. I mentioned that I am concerned about it because I won't have liability insurance until October 1.  He then says I am starting this off as a contentious relationship.  He cited that when we negotiated the lease I was difficult then too.  I actually gave him several exceptions to the boiler plate language that is standard here and 99% of landlords and property management companies will not negotiate.  I told him I felt I was very reasonable and I gave him several exceptions that most people would never consider.  

To be reasonable I said I would talk to my insurance company and see what they said.  To be legit I think I have to change the lease and the start date of my insurance to match September 29th.  I want to tell him the lease is October 1 and you can move in October 1 or it's trespassing.  It is slightly complicated because we are moving a small distance away and I can't think of a good way to give him the keys October 1.  

Am I being a difficult landlord by insisting he not move in early?

Do some tenants just want to negotiate and argue everything?