I personally don't feel comfortable outsourcing this to another person.

I want to know if it is a good idea to outsource all of the things that come with owning a rental up front meaning should I pay a property management company up front?  

I think what he is probably looking for is another out source marketing arm..

Many investors will, at some point as their portfolio grows, determine that time has become their constraint and outsource the management and maintenance to allow them to continue growing their portfolio and/or focus on more profitable uses of their time.That is why it is wise to factor it into your calculations from the beginning.

But I now have an understanding of those processes and can outsource them.  

Yes Pay a VA to do it or hire someone on an out sourcing sight to do it for you. 

I'm in the process of trying to create systems or outsource most of what can be done that way, that I don't want to, or would prefer not to spend the time doing.

or read somewhere that when you first get started, you should self-manage to learn what you're doing before outsourcing.

We are NOT looking to do this ourselves but outsource it to someone.

After that, you could outsource and hire a manager to do the management.The flipside of having the power to control everything is that can be alot of work (and a full-time job if you are putting in sweat equity...which you wouldn't be doing).