We have a high saturation of rentals that has caused the market to lose money. 

We bought a property that we feel is assessed by the our local government too high.

If you're in MKE, then you'll probably want to connect with @Shawn Ackerman.Do you a price range you're targeting and are you looking for a turn-key property or something along the lines of a "fixer upper"?

My thoughts are current housing supply + high rates + high home prices in OR are restricting our options and liquidating the brokerage to pay off the townhouse = $400k asset + $2,400 cash flow that we could then use to leverage or save into buying another property outright or scale into 4 plex and use the rent to pay down that mortgage too.

I highly recommend investing in a property management software, such as Hospitable, for syncing your calendar, automating messaging, and scheduling cleans, as well as a dynamic pricing tool, such as PriceLabs, for optimizing your pricing based on market demand, local events, and seasonality. 

I looked at their booking calendar one time and thought it was pretty empty.I guess you don't know until you try...and probably depends on if you want high occupancy or high rate?

In the midwest, prices are lower.  

For instance, the area closest to Disney is actually less saturated and has many homes that can be renovated to a high standard and will book well.A bit further from Disney, in newer communities such as Solara, Windsor at Westside, Windsor Island and others, you can find deals in this market.

Not being able to rent out units usually just means the price is too high for the market. 

My answer would certainly be highly dependent on his own emotional make up, his desire to relax and travel, his willingness to delegate and outsource, etc.