I recommend assessing the late fee that is in the lease and, if no lease, provide the tenant with a letter that outlines your plan for the rent schedule, late fees and eviction filing.  

Affidavits from the owner / property manager should be signed up to date of closing outlining (un)received rents.  

Disturbance calls, outlining what to do in certain situations...ie. a clogged drain or overflowing toilets, etc?

.- When signing a lease make sure you and the tenant have outlined and gone over the responsibilities of both parties clearly.

I told him no again but outlined what a great deal he's getting.

Let me explain how this would work in real life:- Tenant takes landlord to court for no good reason- Landlord shows signed one year lease that outlines a year of pre-payment- Case dismissedIt's not advisable to take a year in advance, but it certainly isn't restricted either.

The OP will also outline his procedure for repairs which is defined within the lease by reciting the paragraph(s) in the lease that deal with written notice required per the lease. 

If they complain about this, then the fees as outlined in the lease they signed stand.2. 

I can however say that the scenario you outline is not a wholesome one - agreeing to one rate and then paying some kind of supplement on the side.

Immediately proceed by giving notice as outlined in state regulations.