You don't have to flip to be a successful investor
Just like the stock market, you need to buy low and sell high. But in real estate, you don't ever have to sell because a smart investment property gives you income every month! However, you can't start buying when everyone else is because you don't want to overpay for a property like many did. Chicago is currently in a down market that is starting to level out. This means we will be approaching a bottom market, which could last a couple years. For sellers that need to EXIT their property right away, you probably should list now since prices won't be going up for a while and it's busy now. If you don't plan to move and aren't in financial trouble, then hold onto it by all means.
For buyers, you need to first figure out what you can afford for ALL of your monthly costs will be like mortgage, taxes, insurance, HOA's, maintenance etc. If you will be living there, but still are looking for income from the property, then consider a 2 bedroom, duplex, or multi-family building where you can rent out the extra bedroom, floor, unit etc. to cover your expenses. However, not all properties are a good fit for this situation because the monthly costs are different for every property depending on the factors I listed above. The best investment properties are usually in middle class areas where you can get quality renters and the purchase price isn't too expensive.
A lot of people are wondering whether to invest in transtitioning neighborhoods right now, and I say YES! These are great areas to find great deals right now and the property values should only rise, but I only recommend buying in these areas in bottom markets because these areas usually struggle in down economies. Rogers Park and Humboldt Park are prime examples of this. Also, only buy in areas that you feel comfortable being in. You may need to visit the property to collect rent, do maintenance or even live there. As a result, it should be an area that you would feel comfortable being in at all hours of the day. Two major neighborhood features that turn me off personally are vacant lots and boarded up homes. Those are signs to me that this is an unstable area, which makes it a risky investment. Finally, I would also check out the local businesses or lack there of. If "Main Street" is also empty and boarded up, then that may also be a bad sign.
Well I hope this blog post was helpful. Contact me directly with any questions!