I sync my outlook calendar (2-way) with my gmail calendar, then use that calendar on my phone any changes I make sync to my gmail which later sync to my outlook.
For POP3 email I have my outlook not delete from server until I delete the email, I have gmail doing the same thing (I use 3 separate pop3 accounts). This allows me to get emails in both places, I also have my gmail imap'd into my outlook so I can clean it up from there.
As for contacts I just export and import manually gmail to PC and vice. If anyone knows of a remote sync let me know.
I am not near my PC a lot and this has allowed me to have it fully up to date when I get home, but also allows me to keep minimal emails on my phone and still have them on my PC. I am not sure if these option will work for you, but they works well for me.
On another note I use a gmail account that I don't use for any other reason, the e-mail is set up to use my primary e-mail and not my gmail for returns. (This make it so when I reply it is sent on behalf of my primary account by my gmail account and any replies to this email do not go to the gmail account, but the primary one.) I hope that made sense.