Vinyl Siding On Rental Property?

I have a repair guy that wants to put Vinyl on a rental property of mine. He said that would be the way to go rather than the smart siding. All the wood looks to be rotted on th outside and I do have this up for sale. Would it be okay to just lay over this rather than tear into it? I don't really want to go through more expense if I don't have to. Does the City allow that & does he have to get a permit to do this? I need 200 sheets for $1,500 & $300 for the trim. His labor is $2,200. I also have hugh arch windows in the front and the building is shifting on the B unit, so wouldn't this come apart & tear the caulking apart as well in time because of the shifting? This is a duplex and this is for one side only.