I shall post the entire process here when I do start the project to hopefully shed some light to everyone who is thinking of doing the same project and share the lessons that I will learn along the way as well as obtain feedback and suggestions from others.

Also I have the book on Long-Distance Real Estate Investing (along with many other real estate books From referrals and Podcast mentions) which on shed light on the pros and cons of out of state investing and now would like to put it to the test, being that I have about 50k to invest and looking to starting obtaining my real estate goals.

Also there are two decent sheds in the backyard for storage.

Would any real estate attorneys who practice in Illinois and have a background in tax assessment and reclassifying property types be able to shed some light on this area for me?

I bet @Chris Mason  can shed some light on this.from my perspective and i have been 1099 or self employed from day one of getting in real estate 44 years ago. when i am making good money that shows positive net income on my tax returns I can get a loan for my personal resi ( best rates) and investment loans 10 mortgages  like most folks.. after that its community banks.. and again no problem as long as your profitable. 

Happy to shed some light if you have any questions.

The big shed is custom-painted in Broncos colors orange and blue.

I just bought @Amanda Han 's new book and according to the video that came with it the 20% pass through will apply to shed e income regardless of how its owned.

Shed some light on that for me, when possible.  

Can you shed some detail on the house you let go.