I've purchased a few units online and they don't require any sort of licensing. 

I am looking for tips on structuring a rent to own deal.  

Originally posted by @Allen Underwood:I highly recommend visiting a few local banks versus working with a chain- Especially if you are looking to leverage with non-recourse loans. 

She used a lot of private lenders and wasn't a high income earner.  

You shouldn't expect to purchase things online and then claim that they were in fact an error.

Is it the high upfront costs, finding a reliable lender, or something else entirely?

May I ask if you have a realtor recommendation?

A few tips on the website and on meeting some fellow investors:Search for local meetups here or google a local REI club to network with other investors.

Use that money to invest before you sell the condo.The Chicago market isn't dropping anytime soon...inventory is still DRASTICALLY LOW and rates are still high. 

High interest rates and dwindling capital reserves have led smaller investors, who have long driven the market, to pull back.Shift in Investor BehaviorFor years, individual investors fueled price growth through small-dollar deals, but rising interest rates have made them less aggressive.