Will I lose root & CWM when I upgrade via Kies (Galaxy Note 2)? I rooted my Samsung Galaxy Note 2 with ClockworkMod Recovery. My Samsung Galaxy Note 2 is using Official Samsung firmware from T-Mobile and ClockworkMod Recovery.

In the future Samsung may release a new firmware update for my phone. If I update firmware using Samsung Kies, is it possible? will I lose root? how about the recovery? does it go back to the original recovery instead of ClockworkMod Recovery?
Yes, you will lose root (OTA survival mode at root application does not always work).

Recovery loss depends on package, provided with upgrade (it varies on availability of recovery.img).