It also depends what you mean by experienced.

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.

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

You might have additional items depending on your market.1. 

It depends!

Be prepared for trial runs with several different candidates if you choose to hire a handyman to make sure they turn out to be qualified and dependable.

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.

Your visits to the home seem to upset him, if you don't enter his room and your son is living there depending on the lease wording there probably isn't a violation.

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!