Sounded like there was heavy paperwork involved.  

Companies that know what they're doing don't get involved with the race to the bottom. 

I was heavy in RE but sold most in 2021 and appreciate the simplicity of a Vanguard TSM account as I head into the last 5 years before retirement. 

For example, you might agree to a 70/30 or 60/40 split, depending on his level of involvement.

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.

There are also additional costs of operating and maintaining an LLC, like separate bank accounts, annual report filings, tax filings, etc.2.

It may be easy to rectify, maybe not, depends on your jurisdiction, the issues involved and the City's stance. 

And lastly, market risks and mismanaged funds can also create major headaches, especially for those involved in lending groups.

My mortgage will be $2,005/month, and I’m budgeting up to $600/month for utilities, leaving a potential monthly cash flow of $995.I also set up an LLC and a business account to track rental income and expenses.Questions:Do you have any advice for me as a young real estate investor?

So if your interest payment is $1000 then the servicer automatically ACH debits your account that plus the servicing fee (assuming you set up automatic payments as @Christian Ehlers suggests).