If your debt to income ratio is good, you can control a $700-800k asset with $50k.

At least we don’t have rent control and it’s in the IL constitution that rent control is illegal otherwise Chicago would for sure have it by now.

What are some considerations in finding a provider that offers checkbook control?

With the purchase option Bob has total control doesn't he. 

Like you I also have the RE license to keep some of the commissions and better control. 

This works well if it's an MTR or STR type situation and you are in control of the lock.

Less waste, more controlled environment, less surprises. 

After that's under control, focus on increasing income through additional work at your current job, taking on a side hustle, or finding ways to increase income on your existing rental.At the same time, educate yourself.

That bet didn't pay...At the end of the day, deportations and tariffs are things us RE investors can't control, so instead, focus on things you can control. 

It's a shared house so they have no renter's rights giving the owner huge leverage and control.