My first thought is your zip code... east coast? You need guidance, i.e. what are your thoughts on being an absentee landlord? Will you hire someone to take care of your investment locally?
Where to buy depends a great deal on the amount of your investment. If it is a condo and all other things being correct to support the condo investment, make it a 1BR for mass appeal while minimizing potential for the tenant to increase occupancy.
It's the best time right now to make an investment in Chicago due to our market warmth vs. chill in other areas of the county, low rates and inventory at the top end of the range. There are fewer advantages to wait later in the year over the benefits of making the investment now.
The rental market is going through the gears since tightening of money and tougher guidelines for first time buyers to qualify. College grads come to Chicago enmass from surrounding states to see what's it like to live here... read 'fun' and it's a great corporate center for entry level positions as well as specialty top grads to get the offers the expect.
Value in 10 years... it's guidance again, a different way of thinking, you make your money when you buy. Your 10 year goal is bright thinking, It's difficult to make back the buyer closing costs and attorney fee, add sales closing, commission and attorney costs in less than 4 years. If the market is so hot as to allow you to sell and buy up in less than 3 years, it's guidance with intimate knowledge of the market.
Net... do not make your first investment as an absentee landlord.