What I have read so far on the web is that there is no way to add a reserved IP to an existing VM (unless I recreate the VM which I am trying to avoid). However, I have noticed
Find the Resource Group (RG) where your VM is Located
Confirm your VM has a network interface - if not, create one (it should have one)
Create a Public IP Address (static or dynamic, doesn't matter) by adding one to your RG from the marketplace (do this first so it is creating while you make your NSG).
Create a Network Service Group by adding one to your RG from the marketplace and associating it with your VM.
Once the NSG has deployed, go back to the Overview of your PIP and click the "Associate" button in the info section of the blade.
Select the Network Interface of your VM you validated in step 3.
Get a cup of coffee or something, it will be a minute, but otherwise you're done.