email via wifi

[Icthus]

I posted this in the wireless forum as well, but have not received a reply:

I am currently using a TG50, but have a TH55 on the way. I have never used wireless, but have many wifi hotspots around. I use Outlook for all of my email, and am currently using Beyond Contacts to sync with Outlook, to include my inbox.
Outlook is setup to remove messages form the server, so when I send/receive, the messages are on my hard drive and are no longer on the server.
It is important to me that sent messages get copied to my sent folder in Outlook. My questions are:

-If I download messages to the Clie via wifi, will I run into problems later when I sync with Outlook (since I already have the email on my Clie, and Outlook is pulling teh email from the server)?
-if I send messages from the Clie, will they be copied to the sent messages folder in Outlook?
-What would be the best email app to use for this? (I can already open attachments in DocToGo 6)
-would it be "easier" to handle these things form the desktop via a VPN client?

Thank you for your answers.


James