I don't think the build process is a pita at all, but to address your
points...

1. Wrong NAnt on path
    I usually include the necessary toolset in the source repository.
It would be as easy as putting nant in a tools\ folder and including a
nant.bat in the root.

2. System customization to run tests
   This could be solved by including a custom nant task to create db's
on the local machine. Again, much easier if you include nant with the
src.
   Also could be addressed by writing custom attributes for NUnit to
detect and decide if the db is installed.
   Something like [Required(MSSQL2005)]

3. Building w/ Visual Studio vs nant
   I haven't found a good solution to this one. Is it possible to have
VS run a custom build script instead of its own?

4. Human Errors -- "works on my machine"
   CI and Gated Check-ins. :)

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