You can see the statistics of DOM and properties on the market are trending strongly upward.Consider the monthly assessment and the financial strength of the condo association.

I don't know which part of Wisconsin you are in, but the Milwaukee market has been running on 22 DOM (days on market) this summer on average and now trending into the mid 30's in fall - just for perspective: 180 days used to be normal. 

All good advice.A trend I've noticed here (example):  House lists for $91,000. 

According the graph below using the inflation adjusted trend line you can see that over 45 years the average value has increased from 150k to 180k.

Parents like this but again my accountant hates it (starting to see a trend?).

Higher prices + Stagnant Rent = Lower Returns.I'm not sure the best way to navigate this trend other than ride it out through long-term holds. 

Kansas City has shown great population growth, job growth, median HH income growth, and crime is on a downward trend.

I highly recommend utilizing Neal Bawa's Real Estate Trends spreadsheet. 

Other than looking at numbers and trends within those numbers, I go to the area and have lunch or a beer.

That includes the books, which contain a number of highly detailed rehab costs/trends/spreadsheets/etc.