> I got the impression that they were happy sheeple using MS's stuff, and
> might try out some OS/FS here and there.

Im not so sure its sheep mentality as it is, 'no one ever got fired for
choosing Microsoft'.

> Judging from the frequent "page not founds", ASP/ODBC/SQL errors and
> speed of their various sites, I'd say they have great job security at
> least.

Can you provide a list of these errors or pages?  I am sure their
webmasters would love to fix any problems you are finding.  Specifically
if there are short comings in the technology proof of it can only help
your cause in conveying to the leadership there of the problems.

> Unless there is a change in leadership, I doubt you'll see much change.

While this probably rings true in most cases, drivers are also important. 
If you read the news papers its evident the state budget is hosed.  BADLY.
 Because the county is not a charter government (meaning most of their
revenues depend on others (i.e. the state), you can expect things to
trickle down and trickle down fast.  This 'driver' likely might sway
opinions of leadership in some cases.
>
> Sorry to seem sarcastic, but I get irate knowing that they are wasting
> my tax dollars on stuff that could be done SOOO much cheaper.

I question the SOOO cheaper.  Freedom is expensive.  I would suspect
switching away from Microsoft would likely actually be more expensive in
the first year or two, but real dividends could be realized by a
significant number in the 5 to 10 year outlook.

However, a phased rollout/replacement model could reap benefits smaller in
number over a period of years without raising costs.

-derek