Which side should I move into?

[Jim Davis]

I am looking at purchasing a duplex. One side has a long term tenant who is paying at least $100 below market rent, but I wouldn't call them a dream tenant. There is obvious water damage on the ceiling and near the shower and the bathroom the floor below. The leaks may be taken care of already, but at the very least some new paint is needed. If they were long term I'd hope that they'd at least want to have those things taken care of and let the owner know. It seems they don't mind.

The other side looks amazing and is renting at or slightly below market rent.

My plan is to move into the side that needs some work and keep the immaculate one open because it seems much easier to rent, + I don't mind living in the side that needs a little work and doing some of it myself. The problem is most of the people I've talked to think it's better to keep a long term tenant. I agree to an extent, but this property is pretty nice, and in good shape so I want someone living there who wants to keep it that way by making sure problems get taken care of.

If you are starting out and had to choose which side to live in which would you choose? By the way, the worse side is actually pretty nice too it just needs some fixes here and there.