.$1400 is definitely doableI wouldn't hire property manager- just post it on military by owner and ahrn.com and your vacany rate will be low.

Welcome to BiggerPockets, @Kevin McElhaney.Are you planning on doing the work yourself, or are you hiring it out? 

Also I plan on becoming an agent in the future because when I get a handle on flipping, I can keep that commission instead of paying that realtor I would need to hire to sell that flip, so it makes sense in the long run. 

If the PM has horrible communication timelines and abilities while he is trying to get my business, I can only imagine how much worse it would be when I actually hire him to do the job.

I was recently approached by a company looking for an outside sales rep (account manager).1- I can see how this position will offer me the more freedom to structure my days to fit both my real estate deals and my sales clients. 2- It also involves travelling around the country, which might give me the opportunity to learn other real estate markets to expand the areas in which I do business????

What I don't know I will research, and what I can't do I will hire an expert.   

Hire an engineer to help you draft specifications and a create a solid contract that dictates pay apps.  

Since there will be a total of 27 properties to take care of and I really enjoy my job, I'm not sure if I should hire a property manager to take care of the properties and keep my job with benefits or quit my job and just focus on the 27 properties myself and that would be my full time job.

If he is an owner he should consider hiring an industrial broker.  

If the only person willing to serve is the most incompetent person in the association, that reflects on the owners standing by watching it all go down. 4) She's clearly violating the stated CC&Rs but unless the owners do something about it she's going to continue to do it regardless of what the law or CC&Rs say. 5) Hire professional management - no more self managed, it clearly doesn't work in this community.