This tenant has been a pain in the *** and high maintenance from the get go, but we are stuck with them.  

I honestly should have more money saved up considering my years of working full-time, however younger financial mistakes have been a painful lesson and I regret not purchasing a property sooner/younger.My most important and immediate goal right now is to purchase a property.I am in (what I perceive to be) a relatively high cost real estate area. 

It can definitely be done.

Ideal for various uses: Features over 6,331+ sq ft of living space, expandable to 12,000 sq ft.

There is both great cash flow and appreciation markets within ChicagoNow with all that said Chicago FOR SURE has it's challenges, but I have found personally that if I lean on #1, my network, that a lot of those high risks go away or can at least be mitigated.

@Nick BednarczykI think people also need to understand that fed rates are not directly correlated to mortgage ratesMortgage rates are more in line with the 10 year treasury which could remain high if we continue to spend money like a drunken sailor

Buying units where I am is often owned by older landlords that have left the rent very low. To create cashflow after rehab the rent is increased to market price and that tenant is unable to afford new rent. 
I know i...

Check out this on their site, if you think 50th percentile pricing is too high, you may want to try pricing at 25% and see how that looks.  

In the case where the Seller still had an outstanding mortgage, this would NOT be called traditional "Seller-Financed" (rather Subject-to) and has way different contracts and definite risks involved, such as you mentioned.. and others like the due on sale clause which accelerates the full mortgage due if the original lender finds out the house was sold to another end buyer without them getting their mortgage paid off first. 

I highly recommend that even if you combine lists, you still have a way to know where each contact came from originally for more effective marketing and targeted messaging.