Also your ceiling for increasing rents goes up because you have more units that you can bump rents on.

I feel the top of the market in the West Bend area is about $800 per unit for a duplex and $1,600 for a SFH so I am keeping my ceiling around $160k.

Both are on the ceiling.  

It works well for repairs.One tip though is use only flat paint on the ceiling and walls as flat finishes do not show imperfections like glossier finishes. 

Look at the roof ridge, any sagging or cracked walls/ceilings.5) Roof - KInda obvious, but they are getting expensive.6) Open permits or non-permitted work - Call the City and ask for permit history.

Owner occupied houses have much softer ceilings.

To do so, add a floor to ceiling kinda door.

It's been repaired esthetically (new paint, crown molding, ceiling fans) but none of the major problems have been addressed.  

How tall is ceiling in the garage?

Additionally, the use of ceiling fans in these areas can further assist in distributing conditioned air more evenly throughout the house.