To Rent or To Sell? A Condo Owner’s Dilemma

[Rahul Raghav]

Hello, everyone. I am a new condo owner in South Loop, Chicago. I bought a 2-bedroom condo in this area this year (2023), after renting for 11 years. I thought it was a good investment (for renting it out after living for first year), but now I am having second thoughts.

My condo has a high monthly HOA fee of $700, which covers amenities like a gym, and a doorman. The maximum rent I can get for my 2-bedroom condo is around $3,000, which is barely enough to cover my mortgage, taxes, insurance, and HOA fee. That means I will have a negative cash flow if I rent it out.

On the other hand, if I sell it now, I will likely lose money on the deal. I bought my condo for $400,000 last year, and I still owe $360,000 on my mortgage. I will also have to pay capital gains tax on any profit I make from the sale, since I have not lived in the condo for at least two years.

So, what should I do? Should I rent it out at a loss or sell it at a loss or no profit next year (long term capital gain tax)? I would love to hear your opinions and advice on this matter.

Thank you