Is there a way I can run 'sudo dpkg-reconfigure dump1090-mutability' with the '--force-confask' option (I guess I could have tried that), or could you build that function into the reconfigure so it will ask if I want to replace the conf files? Thanks.
It's a function of the package upgrade, not the reconfiguration.
The javascript/html are marked as "config files" so that
user modifications are preserved. They don't actually hold config information and they are not touched by dpkg-reconfigure at all.
When a new version of a package is installed, dpkg looks to see if (a) the config files have changed between the two package versions and (b) whether the current version of the config file is different to the original "old" version provided by the package, i.e. has been edited by the user. If both are true (I think that's the rule, anyway) then it will ask you what you want to do about it. If the config files haven't changed, or if you haven't made modifications, then nothing is asked and the files are left untouched. If the config files
have changed but there were no user modifications, then dpkg installs the new version without asking.
Further complicating things is that when you turn a non-config-file into a config-file, that looks to dpkg like the file was user-modified. So when I made that change, everyone got a prompt asking what to do about those files.
The problem arises when you say "no don't update the file". At this point you've taken on responsibility for making it work with the new version. But invariably that doesn't happen and I get a bug report.. At this point merely reinstalling the same version doesn't help because condition (a) above isn't satisfied - if you're reinstalling the same version, the config files haven't changed between versions at all. That's what the --force-confask on reinstall is about - it overrides the first condition and asks you again about every config file.
The alternative for the user is to go and find the new copy of the config file, which dpkg will have left as <filename>.dpkg-new, and use that. But it's simpler from my point of view to just have a magic command that fixes it rather than trying to explain how to find and rename the right file.
The other way to solve this problem is not to mark the files as config files at all. Then installing a new version of the package will unconditionally replace the existing files with the new copies - regardless of if you made changes. That's easier for me but not so friendly for users as it seems like modifying the webmap is a popular pastime..
TL;DR: supporting packages when your target userbase has no knowledge of system administration is a right pain..