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IMAP4 won't help you, as it'll still transmit information 'in the clear', while at least a secure HTTP connection would attempt to encrypt the connection between you adn the server. I don't know of any software that'd help you here, not really - the main problem being that if your'e connecting to an outside network, unless they're running similar software, you won't be able to get an 'encrypted connection' like the type you'd want. WPA is closest in terms of providing a (relatively) secure Internet connection, although it's not perfect and I don't see this deployed in public settings like hotel or airport connections, which tend towards WEP or open networks.
The main problem here will be that any information you send to and from the network wirelessly is open to interception and decryption... which means that they could see the stuff on the pages you'd viewed, and theoretically could get your PW, especially if the page itself handles security poorly (including your PW in a cookie it puts into your PDA, as one hypothetical example). What they would see with a sniffer is all the information you're sending and receiving, which would mean they could see the mail you'd accessed, but not necessarily what was in another message unless you opened it, or unless they got your PW.
I don't know how Skype handles encryption, however - or if it's even there, for that matter. In theory, they could collect the packets and extract voice data, but I can't think of how I'd do it off the to p of my head, but this sn't exactly my area of expertise. In your shoes, I'd be more worried about someone pickpocketing the PDA and thus getting access to all your files - that's why they sell file encryption software, after all.
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