They'll produce a title commitment with the requirements they think are necessary to get you insurable title.

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. 

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. 

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

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

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." 

Deals come to you.Here is what a credible website that ranks #1 on Google produces.