Newbie Help - Downtown Chicago

[Charles W.]

Hello Chicago-Land BP Community!

My name is Charlie and I am new to BiggerPockets. I have been using the great info on this website to get up to speed and was wondering if anyone out there could offer insight into my situation...

I bought my  condo in the West Loop in late 2016 and have been living there with my new wife there ever since. We will be looking to upgrade into a larger space in the next year or two as we welcome our first child. I have been looking into potentially renting our condo out after our next move and BP has provided a solid base. Here are some questions that have crossed my mind?

First off, what should I be using as my monthly repair estimate, CapEx estimate, Vacancy rate estimate, Property management estimate? I don't want to overestimate(my Cap Rate is not great), but I certainly don't want to underestimate either. The space is about 1000 sqft.

The larger question is does anyone have experience renting out condos in these expensive/competitive neighborhoods? The margins seem slim at best. Anything I should be aware of?

Furthermore, what would be a logical next step for me and my family? I don't think multi-family would work for us. I am thinking a larger condo or a town home near the downtown with the plan to move again with the plan to move 1-2 years after that.  Am i crazy? 

Any insight is appreciated. Constructive criticism is more than welcome.

Sincerely,

Charlie