Slow and steady wins this race.
I am still organizing and streamlining my entire system but there is significant progress on a weekly basis.
Some things take time, I've organized my plugins on my DAW and that saves a lot of time. Now it is easier to evaluate different plugins according to type (Delay, Reverb, etc.) Evaluation will take time and then more plugins can probably go away forever.
Start simple, easier to solve problems with fewer variables.
I don't do Windows so no help there, sorry. I've had great luck with doing a search for my question and adding the word "forum". Often this brings up forums where the problem is discussed and somebody who knows how to solve it will chime in. If you get stuck, give it a try!
I have had a Mac system as well. Thanks for the reply amigo.