One thing I would suggest is if you start getting some consistent bookings do not jack your prices up over 15% as a new listing.

Quote from @Stetson Oates: As a suggestion, when you refer to net cashflow, I would include maintenance, vacancy, and repairs. 

Renting it as a standard unit might bring in $2,500/month.

Quote from @Jeff Roth: Hi Lina from Texas-Congratulations on your interest in investing in mid-term rentals and you are wondering how and where to get started.I get this question frequently from investors.Sometimes and investor is looking to keep their property cashflow positive as insurance and taxes have squeezed cashflow by turning units into mid-term or short-term rentals.First off, ideally, the property will cashflow as a long-term rental should something disrupt the mid-term rental model.You will also want to have the property be near where there would be a demand for mid-term rentals (hospitals, universities, research centers).Monthly rents for mid-term rentals are about 20% (+/-) higher than unfurnished similar long-term rentals.There are property managers that will manage mid-term rentals for you and I always advise my clients to use property managers to keep their investment as passive as possible and for compliance issues related to Fair Housing Laws and local regulations.To Your Success! 

Also, coming from running a business just think of RE as a business (which it is), the numbers have to work and your investments need to fit into the big picture.

I'm currently with an investment brokerage at the moment but I definitely want to end up as a investor in the end 

I have never been able to utilize any DPA with any deal as of now, but it is fun to keep it as a possible tool for use in the right situation. 

I think I will not let him make this upgrade as a 5 year payoff would require over $100/month additional rent.  

Now less than a year later, the property is being sold as a duplex and everything on the city and county’s website said duplex.

Don't spend your time with other agents as a focus.