@Robert Obniski In the South I'd explore Hyde Park & Kenwood;  On the Northside explore Lincoln Park & Logan Square, on Far Northside explore Rodgers Park; Near West Side Greektown, Little Italy, Tri-Taylor, Pilsen.  

About 2 years ago I purchased the ugly 600 square foot house next door to my parents.

I've heard this can be a big red flag for an audit.  

You've got to adjust your strategy to fit your market- you are trying to shove a round peg in a square hole and that's why you are getting frustrated. 

Purchase InfoPurchase Price $660,000- First Mortgage -$462,000- Second Mortgage -$0= Downpayment $198,000+ Buying Costs $13,200+ Initial Improvements $10,000= Initial Cash Invested $221,200Square Feet (21 Units) 14,250Cost per Square Foot $46Monthly Rent per Square Foot $0.82Cost per Unit $31,429Average Monthly Rent per Unit $557Mortgages First SecondLoan-To-Cost Ratio 70% 0%Loan-To-Value Ratio 70% 0%Loan Amount $462,000 $0Loan Type AmortizingTerm 30 YearsInterest Rate 6%Payment $2,769.92 $0.00Financial Metrics (Year 1)Annual Gross Rent Multiplier 4.7Operating Expense Ratio 35.9%Debt Coverage Ratio 2.57Cap Rate (Purchase Price) 13.0%Cash on Cash Return 23.6%Income Monthly AnnualGross Rent $11,700 $140,400Vacancy Loss -$585 -$7,020Operating Income $11,115 $133,380Expenses (% of Income) Monthly AnnualCleaning & Maintenance (9%) -$1,000 -$12,000Insurance (4%) -$416 -$4,992Management Fees (9%) -$1,000 -$12,004Taxes (7%) -$782 -$9,387Utilities (6%) -$615 -$7,380Garbage Collection (2%) -$176 -$2,108Operating Expenses (36%) -$3,989 -$47,871Net Performance Monthly AnnualNet Operating Income $7,126 $85,509- Mortgage Payments -$2,770 -$33,239- Year 1 Improvements -$0 -$0= Cash Flow $4,356 $52,270

Back to square one: MLS, showings, offers, counter offers and a lot of time lost before the potential closing. 

I will be relocating and maybe adding a couple radiators to reconfigure some rooms, no added square footage.  

What red flags do I need to look for in my title search? 

After it's clamped measure diagonally from corner to corner to make sure it's 'square'.  

Other than a new roof that was 50 squares it has been very low maintenance, so while cash low is low, cash on cash looks impressive.