A neighboring property, similar to my current rental property, is now on the market at the same price I paid two years ago, with comparable rent.

I own a few properties throughout the Chicago suburbs and I'm looking for a new market.

Do they need some "sprucing up" ($2-3k) to get market rents or do they need more extensive renovation. ($10+k)- How is the building appear from the outside?

To answer your question: As for my market (San Diego) there is such a shortage of housing that even with a steady population we have been near nation high in RE appreciation each of the last few years.  

I would think no, and that a refund is owed but I also am not specific to the market. 

Study the market.

People who can share their experiences in different markets or with different investment strategies. 

Identify which market you want to be in and start making connections there.

From my internet sleuthing I knew the owners were in at least their late seventies, lived all the way in Oregon and had owned it for nearly forty years.

Anyone with insight on the market willing to connect?