I'm in a somewhat similar situation, planning to install Vista on three machines in the next month (one at work and two at home). I'm going to do all the inevitable troubleshooting at work - so at least I get paid for shouting angrily at the computer - and write down the trickiest passages of customization needed to make it work like I want it to. It should probably come as no surprise to those who know me that I can be a little... anal about personalization. 

Then I'll repeat the process at home on an older machine (hoping it can stand the OS), and finally transfer all the changes on my main computer, hoping I'll be spared the worst of the headache.
I'll have to set it up so that everything is in English but working with an Italian keyboard, so I'll let you know if I find a quick way to fix this. I'll be using Vista Ultimate SP1, by the way. I remember installing it once before and not having any particular issue with the language aspect of it, though.
And I'm likewise interested in a good foobar2000 configuration (thanks Matse for the tip, I raise you 
 this ) but all the best ones require playlist files which I don't use as of now (and therefore ought to create in big numbers).
I wrote down a list of applications I plan to install on the new machines. Most of them I'm already using and satisfied with. I'm posting it for everyone's amusement. Feel free to: (a) suggest additions or substitutions based on your experience; (b) not mention the obvious clues to my shameful life of digital crime.
   WINDOWS VISTA SP1                                                                   
   
  ADOBE READER 9 - freeware                                                           
   
  CLEANUP! 4.5.2 - freeware                                                                           
   
  DOSBOX 0.72 - freeware                                                                               
   
  EMULE 0.49a - freeware                                                                               
   
  GOOGLE EARTH 4.3 (beta) - freeware                                              
   
  K-LITE CODEC PACK 3.9.5 - freeware                                                               
   
  IRFANVIEW 4.1 – freeware                                                                          
   
  PATHSYNC 0.35 – freeware                                                                         
   
  KEEPASS 1.11 – freeware                                                                             
   
  CCLEANER 2.9 – freeware                                                                            
   
  REGSEEKER 1.55 – freeware                                                           
   
  AD-AWARE 2008 7.1.0.8 - freeware                                                 
   
  MICROSOFT OFFICE 2007                                                                          
   
  MIRC 6.31                                                                                                      
   
  FIREFOX 3.0 - freeware                                                                                 
   
  [Extensions:      Download Statusbar 0.9.6.1
                          TabMix Plus 0.3.6
                          Foxmarks Bookmark Synchronizer 2.0.45]
   
   
  THUNDERBIRD 2.0.0.14 - freeware                                                              
   
  NERO 8 8.0.3.0                                                                                             
   
  TWEAKVI 1.0 1085 - shareware                                                                    
   
  REAL ALTERNATIVE 1.80   - freeware                                                        
   
  WINAMP 5.53 - freeware                                                                              
   
  [Plug-ins:          Album list 2.06]                                                                        
   
  FOOBAR2000 0.9.5.4 – freeware                                                                  
   
  [Plug-ins:          
http://www.fooblog2000.com/category/config/config-fofr]
   
  TAG&RENAME 3.4.6                                                                                   
   
  EXACT AUDIO COPY 0.99 prebeta 4 - freeware                                          
   
  LAME 3.97 - freeware                                                                        
   
  HIJACK THIS! 2.00 - freeware                                                                     
   
  PUTTY 0.60 - freeware                                                                                 
   
  UTORRENT 1.7.7 - freeware                                                                         
   
  WINZIP PRO 11.2                                                                                         
   
  WINRAR 3.71                                                                                              
   
  DVD SHRINK 3.2.0.15 - freeware                                                                
   
  IZARC 3.81 - freeware                                                                                   
   
  DAEMON TOOLS LITE  4.12.4 - freeware                                                  
   
  SPYBOT SEARCH & DESTROY 1.5.2 - freeware                                        
   
  4T TRAY MINIMIZER 4.40   - freeware                                                       
   
  UNLOCKER 1.8.7 - freeware                                                             
   
  VDMSOUND 2.1 - freeware                                                                          
   
  VISTAGLAZZ 1.0 – freeware                                                             
   
  EVEREST ULTIMATE 4.50                                                                          
   
    SPEEDFAN 4.34 - freeware                                                                           
   
  DC++ 0.707 - freeware                                                                                   
   
  DVD REGION + CSS FREE 5.9.8.5                                                             
   
  ITUNES 7.6 + QUICKTIME 7.4.5 - freeware                                               
   
  MP3 GAIN 1.2.5 - freeware                                                                            
   
  ACOUSTICA CD LABEL MAKER 3.17                                                      
   
  WAVE STUDIO - freeware                                                                             
   
  CREATIVE WAVE STUDIO 5 – freeware                                                     
   
  NOKIA PC SUITE 6.86 - freeware                                                                 
   
  CHROME GLASS MOUSE POINTERS - freeware                                      
   
  PHOTOSHOP CS3 EXTENDED                                                                   
    DEFRAGGLER 1.02 – freeware                                                                      
   
  DIRECT VOBSUB 2.37 – freeware                                                               
   
  JR DIRECTORY PRINTER – freeware