You are smart to want personal experience along with professional experience. With multi-units, this is especially helpful, especially if you plan to be an owner-occupant. Being the owner/occupant of a multi-unit definitely has its unique challenges, but the financial benefits can be pretty rewarding.
How do I know this? Well, I am a Realtor and also the owner/occupant/landlord of a 2-flat with 3 units just north of Lincoln Square that my husband and I bought and rehabbed 7 years ago. We also own several investment rental properties.
There are many things to consider when purchasing multi-units, from cap rate to cost v. value, to financing (investor v. owner-occupied), and much more.
I have a few tools that might be helpful to you in figuring your cost v. return in advance.
As for how to find the right match for you? The best resources for locating a good Realtor is usually word of mouth and referrals from friends. Shared personal experience from others speaks volumes. Most importantly, though, you need to feel a 'connection' with the agent with whom you will be working, and what might be right for others may not always be right for you. Evaluate the experience, the knowledge, and most importantly, go with your gut.
Your timing couldn't be better. Trulia is fairly new and a wonderful source to get to know Realtors like never before. I believe you can find the right person FOR YOU by reading posts and have better results than you would from a friend's personal referral. Your friend may have been lucky and their agent was never challenged. Your friend's agent may have done them a disservice and your friend over paid but won't find out about it until they go to sell. Your friend may be recommending a cousin or another friend out of loyalty instead of quality. I do believe in referrals. I'm just giving you a couple of examples of when they might not help.
The reason you are lucky, is because you can now get inside the head and situations of several Realtors by reading their past answers on this forum. I've been on here for 3 or 4 months now and can tell you without thinking twice about who I would hire on the spot. You might want someone who is always professional and diplomatic or you might want someone who is blunt and tells you the way it is. I don't know which your would prefer or what other traits are important to you. What I do know, is you will be able to tell by clicking on the agent's pictures here and flipping through all of their answers. A word to the wise about doing that, when you click on the question, hold down to open link in a new window. When you start getting to page 3 and beyond and you hit the back button to move to the next question, you will be taken to page 1 instead of page 3 or 13.
By the way, I couldn't find any referrals when I was looking for an agent in Oak Park. I hired two that I ended up having to fire. I interviewed at least 8 others and didn't feel they were good enough. The agents taking the time to post here are ALL better than the agents I interviewed in person. If you ever do need an Oak Park agent, the only one I would use in the future is Pat McGowan.
The best approach is to talk to Realtors that work in the neighborhood you're looking considering. They know the market, the various nuances of the neighborhoods and pricing.
Talk to them on the phone, find out what they've sold and ask how many byuyers they've helped find Investment property.
I look forward to hearing from you via my profile. Good Luck.
The link below to our Trulia Voices Member Search may be of good use to you. You can check out the Real Estate Pros in Chicago and browse through their profiles, questions and answers. It's a great way to learn about their expertise and personalities.
Customer Service Representative
There aer a few Realtors on Trullia who are very knowledgable and specialize in Chicago Northside. I will forward this question to them; and hopefully they will answer your question.
This is self promotion - be forewarned. I do have the experience helping buyers locate multi-unit buildings on the north side of Chicago. I have also listed and sold them for clients. Two of my transactions this year were for the sale of a three unit building on Barry in Lakeview and the purchase of a three unit building on Oakdale in Lakeview. Clients that have used my services were kind enough to write testimonials on my Linked-In home page. The link below takes you to my real esate Blog, and from there you can link to my Linked-In page as well as our company and personal websites. Check out my Biography to read more details. Thank you!