If you use DB Maint Plans, the last tab allows you to log the results to another server. I set up our plans to log to a common server...

I had a similiar problem with failed maint plan jobs along with failed mail - no notification unless I looked in EM or the log files were out of control...

I would also avoid any NT 4 to Win 2K. Just do the SQL2 Upgrade, then backup all, build new box, install SQL2K, restore master and databases. Also...

Just restore from device added during restore. Again just use the unc path name before file name.