Hey man,When your starting out DO NOT spend all your money on software DONT DO IT!!!!!!!!!
A program like n-track from
http://www.fasoft.com
should be all you need to get started for software, and its less than $80. Its uses vst and direct x plugs, and its not some limeted scaled down version either.
There also pro tools free:
http://www.digidesign.com
Then take the money you saved by not getting $300 software, and get something like a microphone, or take a vacation or something.
Now, you say you have the analog chain to your liking. If that is so, Id reccomend looking into nuendo, vegas, cool edit, cubase, logic, cakewalk.
Any of the big ones are going to be good to work with if your willing to pay, it depends on how you want to work wich is something youll need to decide for yourself.
I'll tell ya, everybody has a different opinion, and most people just say whatever they own is the best simply because its what they use. So, try to get a feel for how different programs interface and sound, and what features you need.