Where do I start

I am a vinyl guy.  And really new to this kind of stuff. Recently I have been working from home quite a bit.  Enough so, that I had to stake out space in my home to create an office dedicated to just me and not the rest of the family.  A golden opportunity to try something new.  So, I have decided to create a modest desktop system.  Speakers will most likely be Omega Super 3i (I have a big desk).  I have a host of amplifiers that I could potentially put into play, including Clones 25i, Miniwatt N3, and ASL Tulip 2a3 (really sweet but not desktop ready; would also require a dac with some sort of volume control).  I also, have an iPad, iPod, and Surface 3.  As well as an AppleTv and iMac G5 in other parts of the house.  The laptop I use for work was issued by the company I work for, so I can't consider using it in the mix. I have no idea what the best course of action is.  Can I use the Surface 3 as a Music Server?  Do I utilize the iPad or iPod?  What kind of dac do I need (willing to pay $500 to start and get my feet wet) --of course upgrade in the future if I really get into it.  I will essentially be building a new music library -- my wife thinks my music is stale (read I am getting old) and this would be an opportunity to try some new things. Don't know where to start.  I read some things about using the ipod into a pure i20 (maybe upgrading the power supply) -- but I don't want to go that route without fully considering my options. I would also like to take the time to put my best foot forward in this effort and not just aimlessly experiment.  Your thoughts and suggestions are much appreciated.