While traffic is light right now, Google says driving commutes are currently: 18 minutes to O'Hare, 27 minutes to Midway, 18 minutes to the loop.

I know for a fact I will get this bull under control and ride it home.

If you can't keep control your finances, you are highly unlikely to succeed in real estate investing.

ergo state wide rent control..  

I found out that I'm a terrible passenger on mortgage loans, I tend to a bit of a control freak, so it was hard to sit back and let someone else handle my loan?

To convert to a rental is a business decision, and taxes should not control it, even if their impact is positive.- If you convert #2 to a rental and do no more flips, the Sch C is definitely way to go, unless there is more pertinent information than disclosed in your post.

I am sure I am still going to have to pay my private lender but I just feel like this is totally out of my control I had the house sold and is a rare situation.

She doesn’t have a new agent program setup yet so we both wanted to see what else is out there.My primary reason for obtaining my license is to have more control over buying/selling my own properties.

Check the HUD website, who control FHA, and see if you see anything that suggests FHA loans have been suspended.

If you can't keep control your finances, you are highly unlikely to succeed in real estate investing.