They did their job - you determine the rent amount, not them;  they can advise you, but you make the final decision on rent amount.  

To find condos in Chicago with positive cashflow you're going to look for condos that are either listed with a realtor or For Sale By Owner and review the financials to determine if the cashflow is positive.

The most determining characteristic will be money -- how much do you have?

I would interview other agents in your area to determine if you want to become a real estate agent.

If I have plans to remove or relocate a wall, I’ll identify which direction the floor joists are running to determine whether or not its load bearing.

Important question that helps determine what court this may end up with should it go sideways. 

I've read multiple blogs / websites / youtube videos on how to determine which state is primed for investing and the general consensus is to look for:Population GrowthJob GrowthJob Diversity (More than one major employer)Average Rent PriceAverage Home PriceCrime RateCost of livingMy question is, where do you guys pull these data points from?

Even with that being said it should not take this long in court to determine the validity.

The rest you can determine by the purchasing price.

The way I have learn to determine what rent should be charged for your home is 1 of 2 ways.- 10% minimum of purchase price annually + property taxes (treated as a cap rate on a business)- 15 year monthly mortgage rate + property taxes Any opinions where I should start, or how I can determine what would be good for myself and my wife to start in would be greatly appreciated.