The biggest benefit to this method is you get to keep your incredibly low primary residence interest rate of probably 4.25%. 

I know that doesn't take into account the finish/quality of the homes, but is that method generally accurate? 

I used that method and have explained it in more detail in other threads or in a book.Moment number two – as a broker, I began doing real estate syndications and raising money.

I want to invest in the Chicago market, but it seems so expensive to find a good duplex, triplex, 4plex.Does anyone have any suggestions how to go about securing a good solid first deal?

They will definitely ask for a financial statement form where you list assets, liabilities, debts (secure, non secure), W2, Job status, ... etc.If you don't have anything palpable, they might just ask some front desk person or salesperson call you back.

In response to your question about a purchase with an initial cap of ~5% equating to a great long term investment - equity growth potential is certainly part of it, but I’d argue that the propensity for consistently increasing rental rates and the stability of the overall rental market are an even bigger piece of that puzzle.I can’t really give you a definitive opinion on your specific situation without knowing more about the current make-up of your portfolio or your goals for passive income.With that said,  there are absolutely  methods to reposition equity in high growth potential properties to more income-centric opportunities within our market. 

I have found uncomfortable to be much more lucrative Pick a listFSBOTax Delinquent NOD ProbateNOOEtc...Pick a method to find themOnlineDrive for dollarsDoor knocking Listsource Referral PPCEtc...Get in touchDirect mail(100s of different type)Email Cold call Door knocking Etc...Best of luck!

Secure bank financing on 1 of the houses for $50,000 which would clear his debt.

If you are unable to secure a better price you may want to look at higher deductibles to see if the savings is worthwhile. 

All parties agree that termination of this agreement without prior notice before December 2019 will constitute breach of the tenancy as agree on Page 1, and all security deposits shall be forfeited in favor of the Owner as full Liquidated damages at Owner's option following termination without notice"So.. what are my options?