This is due to the RADIUS request that is sent when you enter enable - what IOS does is send the username $enab15$, hence why you need to add this user to Windows 2000. With TACACS+ you can have both a password and an enable password as part of your 'profile'(?), this isn't there with Radius unfortunately. Even if you use CiscoSecure ACS as the RADIUS Server (and not TACACS+) IOS sends the $enab15$ username when you attempt to enter enable mode.
What you can do is have different password for each of the possible enable levels - i.e. type 'enable 14' and IOS will send the username $enab14$ etc, that way you can give the level 15 enable password to some users and lower privileges to others.
I agree it's not ideal as a disabled user can just login with username $enab15$ etc (if they are smart enough and can see the hole....). The best thing is to have a strict password policy and change the passwords frequently.
Have you set up any logging? I was looking at logging to SQL (or at least to the MSDE2000 engine) but gave up after a while.
Thanks
Andy