If it is way more work and maintenance but cash flowing the same as a smaller unit doesn't make sense, but since you say high maintenance high reward I'm guessing this is one of the best producing properties.  

This comes with time and experience but a book that helped me tremendously (not really a sales book, though) was "Boundaries" by Henry Cloud.The most common challenges for RE Agents early relate to generating leads and focusing on income producing activity.I would consider spending 50-75% of your side-hustle time on income generating activities. 

@Jay HurstSo then is the next talked about rate cuts that could happen in Nov,Dec getting priced in now or in the next few weeks?

I would highly recommend you sell and do a 1031 exchange into something that will produce income, like a rental property.

Last year, the city required a bank statement, which was not overly difficult for me to produce; however, this year the city of Chicago required either a homeowners exemption or a state license showing the exact address and unit for the listed AirBnB. 

This becomes EQUITY, which can be leveraged 4 to 1 to purchase income producing property.4.

Our main issue is that we are getting exhausted with people who say they're cash buyers and can't produce a POF.

Although taxes and purchase price may be more with a multi family the fact that there are multiple units for rent tend to be much more income being produced.   

., assets that tend to produce income for more than a year) are expensed over a specified "useful life." 

The second idea is to add the powder room in between the two bedrooms, making the left bedroom smalle (the primary in this plan is similar to the previous image, I forgot to update the floor plan again, sorry about that).Please tell me what you think, and also I'd appreciate it if you have an innovative idea that you can share that's better than the ones I mentioned above.