If it doesn't affect my bottom line or vision for the overall project I will frequently defer to them and say things like "you are the expert - how would you handle this?"

How did you handle it?

It is nice to know that when your circumstances change, your CPA will be expert enough to realize the change and know the best way to handle it (think of it as insurance).

Extra expenses will be sure to come up; I just want to be sure i'm in a good spot before they do so I can handle them! 

How should rental advertisement be handled with a property manager?

I have a good handle on construction, I have folks that I can get material and labor, etc.  

If I'm in the range, I'll drive by the house to try to get a better handle on repairs to fine tune my MAO.  

Do you hire a management company/companies to handle the properties?

Two reasons: S-corp provides more legal protection and flips are handled totally differently when it comes to taxes (this wasn't happening with my previous accountant). 

While i have never personally managed a property i did work at a company handling property management like tasks for a 186 unit development project while he was building it and got a great crash course while i was there.The main reason that I would like to do commercial is because having a rather large goal of 1000 rental units by the time that I am 40 years old which would be in 12 years from now.