Inherited Tenant / Fighting Eviction / $0 per Month Verbal Lease

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Ok, so I just acquired a 6 unit apartment building in Wisconsin. One of the 6 units had a tenant/manager who was living there free for managing the other 5 apartments and doing maintenance work. I notified the tenant that I would no longer be utilizing his services and started the eviction process giving him 30 days to move out (used a legal process server and also mailed certified letter).

There is no written lease at all, and tenant has lived in building for approximately 10 years. I offered the tenant $500 "cash for keys" if he would move out in two weeks instead of 30 days.

He's asking for more and is threatening that he may fight eviction which could drag it out for months. 

(2013 Wis. Act 76 requires the court to schedule the initial hearing ("joinder conference") within 25 days of when the landlord files the Summons and Complaint. A complete trial has to be finished within 30 days of the initial hearing. Wis. Stats. 799.05(3)(b) & 799.206(3), 2013 Wis. Act 76, Secs. 29 & 34 Eff. for evictions filed after 3/1/14.)

I have no doubt that I'd win eventually and could likely then get the court to make him liable for all court expenses and my attorney fees. Also, after the tenant is evicted, I could schedule a "rent and damages hearing" where the court will decide how much money the tenant owes.

MY QUESTION is, how would the court decide how much rent the tenant owes when his current rent that I inherited is $0? Can I create a new lease for the same rent as other tenants in the building are paying? He wouldn't sign it, but would the court follow it given the situation?

Can I make a lease for a tenant who is staying and possibly fighting eviction even if they don't sign the lease?

I think you're on the right track. If they are on a verbal agreement, you are under no obligation to allow that to continue. In fact, I would have made it a contingency of the original offer that they either move out or sign a new lease and start paying rent. It's too late for that.

They're clearly being unreasonable which shows you've made the right decision by getting rid of them. I suspect the court won't award rent until you have a written agreement that includes a rent charge. All you've done is given notice to vacate so I would stick with that. Get rid of them, don't worry about the lost rent income.