The only correct advice is, "Go talk to a professional."

If you have the time to devote to it, direct to seller methods can be very effective, but will take ultra-patience and intensive work. 

Even if they do not, it’s not your legal responsibility.Long version: It actually depends on your method of payment, and it’s not always clear.Credit card payments: clearly not you problem, no 1099s needed.Zelle payments: you DO need to send 1099s for Zelle payments.PayPal, Venmo and Cash App payments: this is where it gets tricky.

Brandon Turner outlined this method in one of the older podcasts and there are previous posts in the forums.  

Is this interpretation correct?

Converting your condo into an investment property and transferring it into an LLC is a smart move for liability protection.You’re correct that retitling the property involves Chicago’s transfer tax, which can be substantial.

What other methods should I use to acquire another property? 

If I recall correctly, Rent Redi even gives them the option to pay using a credit card. 

Quote from @Ryan Konen: You are correct that comping software like Privy, Propwire, and Propstream primarily rely on public records for their data, such as county assessor records, MLS feeds, and sometimes 3rd party aggregators.

Used houses in the area sell anywhere from $75-125 a square foot.These are long term rentals that I do not plan to sell.I am reading the Rental Property Investing book and implementing the method that focuses on cash flow and that strategy states you need to have $300 cash flow per month, per property.