With the current setup, you have no central management of workstations, and company email is held in off-site, decentralised pst files. How do you go about backing these up, for instance?
Irrespective of whether you go for an SBS solution, you have all sorts of problems managing and protecting your IT resources.
Implementing SBS will certainly be a solution to the issues, but you might equally find that a hosted Exchange and hosted Sharepoint solution will also work for you. Having your own SBS gives you more control of the workstations, which you can manage through SBS's wizards, Group Policy and a (third-party) centralised anti-virus console. Importantly, you also get to store all data centrally, which you can backup properly.
Workstations can use Outlook with RPC over HTTP(S) to connect to the Exchange server wherever they are - they then get full access to Exchange's facilities (email, (shared) calendars, public folders, et al). I'm not sure what you mean by users having to 'dial-in' just to get the domain features - they need an internet connection to get the POP3 or IMAP email anyway, and there's be no extra requirements for Outlook/Exchange. In fact, the workstations don't even have to be domain-joined to use Outlook/Exchange in this way.
With Sharepoint they get collaboration features not available from simple file shares - it is accessed over a (secure) HTTPS connection, so they need nothing more on the workstations than they already have.
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