Should I continue to sell or refinance to lower monthly & rent

[Hope Louisse Montenegro]

Hi everyone, 

I currently own a Condo in downtown Chicago and have been trying to sell it with no success. I listed at 370k without parking (35k) in February as suggested by my realtor and have since lowered it to 325k without parking with a new realtor. I have learned since my purchase of the condo that it is not a great building to be in with the small space, association rules and regulations, no amenities although it is a great location in the financial district with easy access to all transportation. Work has been unstable for me and I want to take the equity and buy a better cash flowing Turnkey property in Indiana. 

I am trying to figure out an alternate plan if I am unable to sell. I had refinanced last year to a 15year 2.75% which makes my monthly including HOA of 475 at about 3k. Since work is unstable I am uncomfortable with the negative cash flow I would be acquiring if I decide to rent it out for market value of 2300-2400k. If I refinance back to a 30 year 3.8% which I was quoted, my payments would lower to just under 2500. I will lessen how much I could be under and cash out 21k I can use for another property.

Or should I just lower my price for sale even more and just cut my losses? 

This is my first post and would love any/all suggestions I could get! 

Thanks so much,

Hope