Next Level with RE Portfolio - When to bring on employees?

[Wes S.]

I have been investing for 10 yrs part time, have built up a decent portfolio of SFH, Duplexes, Fourplexes, Senior Living Complexes and a few Commercial Buildings...the returns are solid but my maintenance and repairs are eating at me - not only money wise but activity wise (calls, complaints, etc.)

Up to this point, I typically hire out to local contractors (plumber and electrician) and do the light maintenance myself, when I can along with a few individuals who help with light painting, fixtures, etc.  I have a very part time asst to help with leases, renewals, paperwork, etc but is pretty limited...

I operate another full time business that is the breadwinner and have a young family ---- so it is becoming more difficult for me to maintain focus with all the action going on and maintain a solid work/life balance.  Basically, I'm looking to duplicate myself!  

My question is for those who have built their portfolio/business to a point where they now have their own employees:

- At what point did you hire Part Time or Full Time Handyman? Manager?  

- How about part or full time in house Property Manager to take care of all paperwork, showings, etc? *I feel hiring an employee to assist with portfolio is a better option as I still want to be involved, have some control and continue to develop/build assets...

- What processes or systems had a dramatic impact or that you'd suggest to improve the efficiency of your daily monitoring, maintenance and performance of your portfolio? 

- Other silver bullet suggestions that made a difference to your business?

My goal is to scale this portfolio/business to a level where it will crank along without me and become the well oiled machine I set out for 10 yrs ago.  

Thanks in advance for your advice/suggestions.