Matt, sorry I don't live near you, and I am not putting myself forward as an expert in JMRI, but as I was in your position 2 years ago I can hopefully give a little advise.
Firstly( and this is a bit of a kick in the nuts), there is no easy route, it's also very addictive, frustrating, and time consuming (possibly covered by the first comment).
What is your normal operating system, gaugemaster? Hornby? Digitrax? Nce? Or have you gone the sprog route, if none of this makes sense then you need to read up a little more on the JMRI download site, if it does make sense then you are on your way.
I have used it with the Gaugemaster prodigy system, but I have set it up with a sprog 3, which to me seems easier to use.
Firstly get comfortable with decoder pro this will help you understand how the system functions ( windows wise ) as although straight forward now, completely baffled me to start with.
Just to give you some idea, I am a novice at a novice stage, I have a drawing of my layout on my laptop and when I click the mouse on the point on the screen the point on the layout operates, at the same time I control my locomotives on either my I pad or mobile phone.
I have yet to 'suss' out how to operate the points from the I pad or mobile phone but it is ongoing.
Sorry to have waffled on but I know what it's like at the beginning.
Good luck!
Ivan