Tenant/Handyman Compensation Built in the lease?

[Matthew Longwell]

Hi, I've made an account just to ask advice on this question. Currently I'm negotiating with a seller who is a contractor and has rehabbed a single-family property. As a side agreement, we are asking him to convert part of the house into a single-bedroom ADU post-sale. He has also asked to for a one-year lease after the sale.

I'm thinking of also asking him to provide building maintenance pro-bono for any small maintenance issue (handyman worthy) that arises on the property and which he is capable and/or qualified of doing. Is this last point complicating things too much? Is it even legal to ask a renter to provide maintenance pro-bono? What would be the tax implications of doing this (would he become a 1099 employee)? Would I have to build the compensation into the amount of rent due or could I actually contract it as a free service he provides? Would it be best to include such a deal in the Rental Agreement, or as a separate contract?

I'm operating in the city of Los Angeles. We are subject to California tenant law. The building was built in 2002 and is not subject to the local rent control ordinance.

[Thomas S.]

First it is always a mistake to rent to a previous owner. Nothing but attitude and bad relations. They have a inflated scenes of ownership that is not desirable in a tenant, don't do it. Second you never ever allow a tenant to do any work on your property. If you want him to do the work hire him, with a well defined contract as you would any contractor.
Do not rent to him, hire him as a contractor if you choose. If you do for some unknown reason rent to him do not hire him or allow him to do any work. Find a different contractor to hire.
Never mix tenants with contracted work or work of any sort on your property. Liability concerns are very real.