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 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?

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

Study the market.

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.

It is OK to lose here and there if the market, the numbers, the investments are slowly but surely going UP.

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.

Anyone with insight on the market willing to connect?