This is super helpful and I can't emphasize enough how this first sub-to purchase has been a lesson in "I don't know what I don't know." 

I will openly admit I did no research into RentRedi or any property management software when I decided to leave Quickbooks I just saw a RentRedi add that showed the Biggerpockets team raving about the software and being a Biggerpockets fan I jumped right in. I

What area of Chicago are you looking to invest in?I

Thats my strategy there ( by way of sqqq calls), basically selling all of my longterm portfolio and building up a war chest of 🤑 to go pick up options that I have a high degree of certainty will make some big gains (thanks to the inside scoop from youtuber meetkevin, I am a course member so I get his trading alerts.)I am sure that was probably a few more paragraphs then you would have wanted haha but yeah hope that helps and feel free to check back in i will be honest about wins and losses.I am really most excited to dig into Kai Andrews' course.Cheers folks! 

I keep track of expenses as they come in (I have a notebook) for each rental and file the invoices/bills/etc as soon as they come in and are paid. 

The only reason I chimed in is a lot of folks might take this as gospel for any and all areas.

I now had someone to give me guidance in all of these new and delicate situations I was finding myself in. I

But you shared a lot to information and im taking it all in. I

In one of my markets I invest in I could buy a house cash for $200,000.

It's reassuring to hear it's not a rare nightmare scenario I'm in. I