You should definitely raise rents each year, and put into long-term leases rent increases. 

I have some properties of Seneca street and the housing prices are increasing but I’m not seeing much growth in the area as far as new business, development, etc. what’s your input on that? 

Values have increased significantly in recent years as higher density development has pushed further from downtown.

How do you account for increases in property taxes (Chicago is more than likely going to increase taxes for the next few years)?

Have you talked to your insurance broker about increasing the deductible?

This is very popular in rentals with hands-off or absentee landlords who don't handle much of their own maintenance.We do business in Pittsburgh, the city proper and the immediate suburbs.

Or, I could use all or some of that cash as a down payment on a place here in CO, but I worry that the market here is increasing at rate that it cannot maintain.

Not only is it a mental and emotional victory, but it increases your cash flow.

Property Radar and List Source seem to be popular sites to get lists of foreclosures and out-of-state owners so those may be good places for you to start.

For moving there as a primary it depends on what you are used to but for investment purposes depending on where you are there's forms of increased development and is a marked for gentrification.