You just have too much time on your hands.
I don't like how Windows does this either, but I just let it go. But for some reason I have a problem where if say I have "The" on an artist, it will be gone on my iPod, or sometimes vise versa. It's really weird. For example, Red Hot Chili Peppers had no "the" on my computer, but on my iPod it did. Really weird.
Ah! Y'see, RHCP would never be a "The" in my current system! :-D
Yes, T&R is superb, especially for that big initial "whipping into shape" of an unruly, dodgily tagged collection; you can alter tags from filenames, alter filenames from tags, etc etc, for multiple files automatically. It saves hours of fiddly work if you're trying to prep your music for an iPod, as I was only recently.
Also, freedb is often inaccurate, but more to the point is inconsistent in formatting. Some people don't know how to use capitals (or, even worse, lower case) and some just can't spell! T&R lets you quickly browse through and nail those problems.
Finally, I have a significant number of single tracks in my collection, mostly recently-released stuff. T&R lets you quickly select all of those and purge their album tags, which removes the hellishly unusable Album listings you can otherwise get on iPod.
You're right, you're right. I really should unplug my ethernet card every now and then and do some real work. ;-)
Sam
PS. Not a huge Eels -fan-, but have you heard "Susan's House"? It's absolute genius. "That must be her sister... right?" :-)
... is T&R free (there's got to be a gag for 'T&A' and 'free' in there somehwere, but i'll leave it before I'm burnt alive at the pc stake)? ... i'm just going thro' the ripping part myself (so slow - still only getting just over 1X speed, but an improvement on the 0.1X speed on my laptop), using EAC/LAME and freedb so may encounter similar problems ... any links? ...
... may give 'susan's house' a try ...
Cheers.
*LOL*... So many gags. Well - T&R is US$25, which I consider really good value. I actually did the bulk of renaming within the trial period, but thought it such an excellent bit of software that I decided to keep it.
The website is: http://www.softpointer.com/tr.htm
Avoid the "current" version, which is 2.x - you want the "beta", which is 3.x. It's much slicker, and I've found it completely stable. Let me know how you get on? :-)
Sam.
Thanks. May give it a go, and I'll let you know if I do (no doubt i'll be back whining about not knowing what a directory is, or something smack-in-the-face-obvious).
ps ... don't want to give you tagging nightmares, but just hope you don't ever have anything by The The in your collection ...

I always go for Firstname Surname - but with classical composers, I tend to leave off their first name and just have the surname in the file. I don't really like commas in my file names for some reason...!
I'm currently ripping a large CD collection, and am tagging all files (using T&R, which I can't recommend highly enough...I think the unorthodox interface works very well once you get used to it) with the following formats:
Cars, The
Flock of Seagulls, A
Folds, Ben
Folds, Ben - Five
Matthews, Dave - Band
Ross, Diana & The Supremes
I know I am swimming upstream a bit here, as I have to edit most of the tags I get from freedb and CDDB, but I can't abide that 300-artist section of "The Aardvarks...The Zombies" on my iPod.
Wonderfully, iTunes' arrival makes this almost immaterial! Yet another way in which it makes life easier.
In the words of the immortal Justin Timberlake, "I'm lovin' it." 
I say you should put "The Who"
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I select my MP3s via Windows Explorer. This goes out to others who do the same - you will no doubt have grappled with the following dilemma:
For bands with "The" in the title, how do you file them?
1. The Who - Won't Get Fooled Again
2. Who, The - Won't Get Fooled Again
3. Who - Won't Get Fooled Again
I can never decide what I really -should- do... The situation is complicated further by the presence of "quasi-the" bands, like Wiseguys, Eels, Sugarhill Gang...
Anyone else find it annoying that Windows "So good for media" XP won't let you ignore the word "The" at the start of an MP3 filename? Or do I just have too much time on my hands? ;-)
Sam.