Server upgrade newbie questions

Question

Hi Everyone!
So I work for a small-ish nonprofit and as I am researching information on what my to-be system is, I am running into a lot of questions.  I have tried google-ing them with not much success.  So I am hoping that all of your expertise might help
drive me in the right direction.
Mind you, I have only been with our organization for about 2.5 weeks, and it is all over the place.
Right now, we have approximately 90 PCs, both desktops and laptops, distributed around 12 counties.  ~50% of these PCs are utilized by our staff, while the others are used by the general public for internet and document editing.  We also have ~
30 smartphones that I need to manage at some level.  I would also mention that we have PCs with XP, Win7, Vista, and Windows 8 (these PCs were all purchased by different people at different times, or donated to our organization).  We are currently
transitioning to google mail, so I was also planning to use the google apps extension to integrate with AD.  Right now, our local "headquarters" is where our servers are located, and the person who set our server up had installed SBS 2011.  There
has been a domain setup, and all but one of the local PCs were added to it (minus the Win8 machine due to SBS limitations).
Because I am new to this, and the situation is a bit complicated (as you can see from above), I was really impressed with Server 2012 R2 because of some of the capabilities of it.  The primary functions of the server are to provide a way for me to manage
all of the users (even the distributed ones), the PCs, and the devices (phones).  The way that I understood this, is that DirectAccess could allow me to provide help desk support (I am the only IT person in our organization so I am wearing multiple hats),
removing the programs that were utilized by my predecessors (i.e. logmein).  I am hoping that with them all added to the domain, I would also be able to ensure that they were being updated properly on a schedule.  We also have multiple different
anti-virus softwares that have been deployed at different times on different OSs.  I was hoping to be able to standardize this and be able to manage that as well.
So....the questions....
Because we are a nonprofit, we are members of techsoup and can get the software cheap enough, but I don't really understand the licensing, particularly the Remote desktop services CALs.  How does this service differ from what I currently understand
as RDC.  Do I need to get one of these CALs to be able to provide remote support to users/PCs?
How do I properly assess the software?  Because I have never performed a server upgrade, or really messed with Server other than seeing the SBS console and being able to muddle through it easy enough, an I going to have issues when upgrading from SBS
2011 (backing up and redeployment)?  The current Hardware is going to be on the low end of the min. sys. requirements.  Is this going to be a huge issue considering the size of our organization? 
Am I even on the right track?  
My hope is to create a semi one time investment (for at least the next few years) so that the focus can be turned towards upgrading field equipment.  
I would appreciate everyones thoughts and help (as I mentioned in the title, I am a newbie at server stuff).
Thanks in advance!

Answer 1

"Because we are a nonprofit, we are members of techsoup and can get the software cheap enough, but I don't really understand the licensing, particularly the Remote desktop services CALs.  How does this service differ from what I currently understand
as RDC.  Do I need to get one of these CALs to be able to provide remote support to users/PCs?"
Your absolute best source of licensing information and clarification is to speak with a trained Microsoft licensing specialist.  You can find one by starting your search at
www.microsoft.com/licensing.
Are all these devices owned by your organization?  If so, dump XP as quickly as possible.  You also might want to check into Office 365 instead of google apps, unless you like the fact that google reads everything you do.  The combination
of Office 365 and Windows Intune might seem like a lot of money up front, but when you consider the significant amount of management time that is simply eliminated by them, they can be quite cost-effective.
It's pretty hard to 'assess' the software without any knowledge of applications needed, usage patterns, vendors, etc.  If you do not feel comfortable performing the function yourself, find a reputable local consultant to come in and assist.
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