Right now I need help finding a contractor that could help me oversee this project and a permitting people to help navigate the whole process. 

Three days without an appointment and someone else filled their seat. 

Also, just from recent experience the STR permit process has become a little more troublesome.  

I am in the process of closing on a 3-bedroom, 2-bathroom, 1600 sq ft single-family home in Akron (zip code 44305).

Any insights on markets with affordable duplexes, good rental demand, and FHA-friendly opportunities would be highly appreciated.Additionally, if you have tips on finding turnkey properties or navigating the FHA financing process for duplexes, I’d love to hear your experiences and advice.Thanks in advance for your valuable insights!

They also allowed a small leak under a bathroom sink go unreported long enough to fill the entire sink vanity to be destroyed by black mold. 

I humbly disagree - it’s all about the process, checklists and the team.  

Full process control start to finish.

If you decide to let your roommates know that you are the landlord, I would also recommend handling the leasing process instead of using an agent to be very clear up front that you are the landlord and roommate of the prospective applicants. 

If the STR is marketed properly this can be very successful, and I've known hosts to fill up the first month or two of availability before the property is ready for guests.