It can make leasing a bit harder since you will have more vacancy when those come do but it will all be in peak season.With respect to the hiring decision, you would need to hire someone to replace you (perform the same functions you currently perform) so that you continue to work up the ladder (spending more time on higher value tasks).  

I'm planning to turn it into a rental and was wondering if I should consider hiring a property manager for my first rental.

@John Reagan Johnson hope you don't mind a PMC answering, but most of our clients hire us because:1) They live out of state and don't have time & expertise to remote manage2) They don't have the time to manage3) They don't feel they have the necessary expertise and/or don't want to risk learning as they go and making an expensive mistake.Go read Kiosaki's Cash Flow Quadrant book.

I personally own a large portfolio here in Memphis and I hired a property manager for the very first proeprty and I still use them today. 

Hire a contractor to cut open the ceiling so it can dry out.

Then hire one that sounds competent and that you can get along with.

There's a self-proclaimed Section 8 guru online who claims he hires random property managers through this website called Thumbtack.

I wonder if there is a way to web scrape for when a new realtor is hired or passed exams in the area so that I could hit them up immediately.  

As RE developers we all know how important it is to hire good, reliable residential contractors. 

Hired a one man’s show property manager after 10 months.