So far used the Linux subsystem on my Chromebook to install GIMP and Filezilla and it actually does work pretty seamlessly. There certainly can be some finnickiness in how the Android and Linux filesystems are entirely sandboxed. They updated the file manager to allow it to enter the subsystems though, so that mitigates most real problems.
Like, i used Filezilla to download a PDF my professor uploaded to the school server, and opened it directly in chrome through the file manager. Pretty good.