Here is my blog on common mistakes when ibuying investment properties.
In Real Estate, 3-5 years is a short-term Investment. You need to consider the costs associated with buying and selling and whether you can recoup such costs in a relatively short period of time based on appreciation rates. Up and coming areas may take time to get noticed and more mature areas with good appreciation may be less affordable.
Alternatively, if you have the ability/knowledge to rehab a property (2/3 flat), that may allow you to take a short term approach to investing where you improve a property, hold it and increase rents and resell within the timeframe you outline hopefully for a profit.
Lincoln Square, Roscoe Village and Lakeview neighborhoods all have upside potential.