Thinking about investing in a 3-4 unit building in Chicago (Jefferson Park, Avondale, Bridgeport, etc.). Is the upcoming winter a good time to do so?

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Timing doesn’t matter as much if you plan to hold for the rent income (also I don’t know anything about that neighborhood). Appreciation is the bonus, the decision should be made on cash flow. Are three units already rented? If not, I would avoid buying later than October, people don’t like to move near holidays. Never lived in Chicago but I imagine people don’t like moving from Dec-Mar

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I think it’s a fine time, you will probably find someone to move in. Sometimes I actually find the winter is easier because there are less places available and renters are more decisive. I believe there is a difference with owner occupied loans once you go from a 3 to a 4 unit. Check with your mortgage person. Also those are vastly different neighborhoods. Figure out where you want to live and take a look at the housing quality, cash flows/appreciation, and potential rental candidates / type of demand. You should definitely try to be close to the train or have covered parking. Also if you can afford it Logan square or Pilsen are hotter neighborhoods for just a little more $ and will prob rent faster and for more. They will prob have less appreciation but better cash flow, better tenants, and easier to rent

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Buying in winter is amazing for the buy side! Im about to close on a property now. The brutal Chicago winter's drive away almost all buyers and the number of transactions comes to a screeching halt. Definitely a great time to buy!

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I am trying to make an investment before I move to DC in 1-1.5y. I the meantime, I can buy the multi unit building as a personal property and move into one of the units. I am just concerned that the timing may not be right and we will see a significant drop over next couple years.

Timing is tough, market is hot not sure if it is worth it if you plan on leaving soon.

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