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I can only really speak to your first point. When imported my existing library, I did it using Sonarr/Radarr as applicable. They have a manual import method, here’s a description of Sonarr’s.
Unfortunately that’ll probably work best if they’re formatted in a way Sonarr can readily recognize, something like /Season ##/S##E## - .ext
. It may take a little work to get there, I found a program called mmv which helps out a lot. It allows you to move files that match a pattern, capture parts of pattern, and use that captured part to name the output file. That allowed me for format entire seasons at a time, but that method does rely on most files having similar names to begin with.
It doesn’t have a speedometer function, but I selfhost Owntracks for personal location tracking with my Android smartphone.
It has a back end that an android app sends location too, and a front end that displays those location points over a map. It can display lines between consecutive points, show a heatmap of the location points, filter location history within windows of time, and more.