You might want to check the FAQ for information on the BB. That is a great place to start.
In order to sync to Outlook, you need (1) Blackberry Enterprise Server (BES) installed by the company (or town/agency in your case) (2) a hosted BES solution such as mailstreet or exchangemy mail (3) BB Desktop manager installed on the PC.
Numbers 1 and 2 allow over the air/wireless sync of contacts and calendar and email delivery. The town or agency would have to allow this. The latter allows for automatic push email to the device and calendar and contact info sync via the PC. Another option, called Redirector, is also available, but it to requires software uploaded to the PC and Outlook running all the time. Plus, IMHO, it isn't a very good option to pursue anyway.
I can't think of any other way to do this.
I don't see it as a good idea to have his company (or in this case town or agency) information on his home computer. The town or agency probably has a reason for their rules and I would not try to circumvent those if he likes the job and desires to stay employed. Many government agencies and companies alike, take their email policies very seriously, even if most of use seems to think it is a bit of overkill on their parts.