Some people just don't get IT... But do you get them?

So I've read about customers that "just don't get IT." All the books and blogs advise you to "fire" the customer that just doesn't get IT. As their "computer guy" you know how to prevent issues. So you install antivirus products on the server(s) and all of the client machines. You use GPO and "make things run" under LUA. You install and configure a firewall. You create backup strategies and policies about how users should do things. You try as you may to educate the users. Oh and of course you enable password policies!

You do all this to prevent a catasphrophe! You do all this because you want to protect that customers investment in their IT. You do all this and much more because you are honestly doing your job! So how does a user see the prompt to change his password every single login each day for 15 days but can not be bothered to change it? I know it is inconvienient but come on - 1 minute it takes - a minute if that - to type your old password and come up with a new one - It's not rocket science guys and you can spare a minute. Mind you this wasn't a problem but do you see how some people just don't get IT?
But I don't want to fire my biggest customer or my main type of customer! Lets face the truth. In the south eastern service industry of blue collar working men it is very refreshing to find someone who gets IT but it just doesn't happen that often. Accountants, Lawyers and other professional services get IT more often. But the guy that drives the work van around town and unclogs your toliet, fixes the appliances, builds your house, manicures your lawn, paints for you - well they just don't get IT and really never will - stop wishing down a wishing well! All they know you do is computers and to them IT and computers are same thing! They operated their business before computers and they don't need them. But it is up to you to explain that business today that doesn't use technology has a disadvantage while those that do get IT will a signifacant advantage over the competition - computers or not!

My current situation: