Most clients use QBO better but want to save money so they use Xero. 

Quote from @William Causey: When choosing a private money lender, how do you weigh the importance of flexible loan terms versus fast closings?

Switching property managers seems like it was a smart move, especially with how much you and your wife had to step in before.Chicago definitely isn’t an easy market, but it sounds like you’re set up for better success moving forward.

They want someone who has the money or can make sure they can get it. 

Kyle, you can fund an entire acquisition with OPM (other people's money).

It's true that you make more money in the long run with appreciation compared to cash flow.

Also, starting my journey in real state investment made change my mindset and since last year I have been more disciplined on my finances and I have been taking better decision on how I spend my money. 

So that's another layer between you and getting your money back and/or paid.  

Terms will most likely not be as good as a DSCR loan but if you needed a quick turnaround to get money in the door for 3-6 months you could go hard money. 

The didn't live within their means, accrued a lot of debt, and it eventually resulted in them not paying rent and being evicted.Consolidating debt reduces their payments so they have more money available, but it doesn't automatically teach them to live within their means.