If they are changing jobs, they need the new job first and you need to paychecks or offer letter with salary or maybe even the first two paychecks at the new job, depending on their level and income.Ask them about deposit and rent. 

Depending where your rental is in Chicago, you should also be flexible with your requirements.

And good to know you have dependable contractor and realtor, that is a silver lining

Depending on your goals, budget somewhere around $3k-$5k per room.

To keep it short and sweet, depending on your deal you should have plenty of options. 

It depends!

Both can save time and improve efficiency, depending on how hands-on you want to be. 

Areas like Aurora, Arvada, and parts of Lakewood or Westminster can be good places to look, depending on your budget and target tenant.If you’re looking for a base hit rather than a home run, focus on finding a property where the numbers work reasonably well as-is—cash flow might not be huge initially, but if you’ve got room to add value and refinance, you’ll build equity to reinvest.

*Eventually* they will come back, which might be in 2 years or 10 depending on how aggressive the tree and bushes are that are nearby.

Yield varies a lot depending on the type of property and location. rental yields for residential property are typically between 4% and 5% per annum.Hope this helps!