They won’t be expecting the same money as their neighbors with the shiny new kitchen and fresh paint.

I'm like, how did the fresh silicone get on there then lol.

I'm like, how did the fresh silicone get on there then lol.

Just get it clean and fresh so they have a nice blank canvas.

This is a development project, so be prepared to fork out meaningful amounts of $ upfront during the process of determining what (if anything) is possible.I would first look through the development standards for a typical R-1 Hillside site (min lot size, length, depth, street frontage etc) and if it looks like you can form a plan that would fit into those requirements and pencil out, then I would tie it up with an extended investigation period and get a surveyor, architect, and some phone calls/emails into city planning.

They won’t be expecting the same money as their neighbors with the shiny new kitchen and fresh paint.

We are removing a wall, changing the fixtures, flooring, cabinets, and some fresh paint.

Maybe you're a bad person, or maybe you're a good person because you're giving them a fresh start elsewhere?  

The three items you mention are pricey, but not that hard to pay someone to do.Have your dad talk to a realtor-not sign any paperwork, to get an idea of market value as is and with the new roof, hot water tank, HVAC, a fresh coat of paint, maybe new kitchen countertops (and hardware), but leaving the bones as is. 

One tenant moved out, we remodeled that unit and moved the renter that was staying into the fresh unit which allowed us to remodel the other unit.