Setting up the VPN should be pretty easy. Your IT support should be able to assist in this, or if no IT support, then there are plenty of good guides - simply search for setting up VPN PDA.
You've mentioned you already have a VPN, so all you need are the settings and passwords.
The web design and mobile aspects, in our case, are totally seperate. We have a business contract with O2 for new handsets every year. We had 6230i's last year, but cheakily went back after 6 months, explained what we were doing and we'd need a adata soultion ASAP and obv their eyes rolled with £ signs. Few days later a load of XDAs arrived - one for each phone we have with them.
It all depends in your case whether you use data now, if not how much you anticipate, and monthlly current mobile spend. All the mobile operators have sales/account advisors who can visit your offices to thrash out what you need, and what they'll give you. Simply ask your business' current mobile provider for a meeting and they'll be there like a shot!
OS side, Windows Mobile 5 is the current flavour of many devices - and powers most mobile/PDA combi devices like the XDA. Although if you go the website route, then the OS shouldn't matter at all. All I suggest is that you ensure your web designer designs in Xhtml and uses CSS to ensure full complience with both PC and mobile devices. The Xhtml route will mean one version which will work on a PC, and a reduced screensize version. Just be sure to carefully select your designer to ensure they have database skills, Xhtml, CSS and importantly experience of making sites viewable on PDA's.
You might find assistance finding a designer at a forum I moderate at. Simply post in the web jobs section of
http://forum.netmag.co.uk