So, the best mapping tool I have used to date is microsoft mappoint,
It ISN'T cheap, usually retailing for 249$ or something, but can be had for much less, check fatwallet or other for deals,

but, there is so much one can do, and it will allow interfacing with external data, (like a client list or such) and then map that data, and still allow queries re: soc econ class, demographics, infrastructure, etc. etc. Works with GPS, comes with MSFT streets and trips and uploads to web and others, and interefaces with all microsoft apps,

again, 250$ or less, but I have found it worthwhile for certain (well, it WAS free)