A (sorry) german Howto sync MM with iTunes and Outlook with iTunes without any loss of music:
http://www.mediamonkey.com/forum/viewto ... 10&t=50145.
Perhaps anyone may translate it.

Musik aus Media Monkey (bei mir flac) nach iTunes (mp3) konvertieren und synchronisieren Randbedingung: es soll auch weiterhin möglich sein Outlook (Kontakte, Termine) zu synchronisieren. Wegen der Randbedingung funktioniert das direkte synchronisieren aus MM gepaart mit dem iTunes-sync nicht. Darum...

Did I really understand you:
I can not sync outlook via iTunes and sync MM-music to my iPhone without loosing my music when I sync iTunes again? There is no solution?

I'm using iTunes 9.0.3 to sync contacts and calendar items with outlook and Media Monkey 3.2.0 to sync music to my iPhone.
It works until I make an itunes sync. After that all my music is deleted.
"Manually manage music and videos" is checked in iTunes.

Any idea how to fix that problem?