Conshe admitted he and his Fiance both have feloniesThey have a Dog (husky)No prior rental history (lived with his fiance's mom)fairly young (27) ProsThey both work (will offer references) (combined they make over 3x the rent)willing to pay asking price (I listed it about $100-$200 more than I thought Id get)He seemed well spoken and maturethey have a 2 year oldHe said his credit score is about 650 (i'll fact check this later)Am I looking for trouble here?

Try the credit unions. 

After the home was purchased with a loan, there was a series of second mortgages and even a line of credit for 300k as late as 2015.

Johnny is going to have to get rid of his lien and clean up his credit in order to get financingThe other option is to fix and flip the property but getting hard $ may still be an issue as many still look at your credit and your experience

I also reached out to a few local credit unions, people's local home equity, and wintrust.  

Had the money for down payment and repairs but with lack of credit history I couldn’t get approved by the bank so I had to get creative.

My intention of paying cash for at least my initial property is that I am in the process of raising my credit score.

To give them credit, they would always send one of the maintenance people within 24 hours, but they NEVER fixed the main problems with the HVAC system. 

I've looked into getting home-equity lines of credit and that seems pretty interesting, but not sure if it wouldn't be better to just use the 30k and get a mortgage and hang on to my equity for later usageI also looked into cash out refinancing.

So, mid term, it's about building a down payment and keeping the credit up.If you are buying as an investment, then there are investment options available.A duplex isn't a great option because living in one side will make it harder to cash flow.