Trisquel is not a rolling release. But you do not have to wipe your HDD - as long as you install software only from the official repository you should be able to update the distro number without reinstalling. I updated from 4.5 to 5.0 without problems.

As far flash videos go: there is a greasemonkey skript, Linterna Magica. Install greasemonkey, then search for Linterna Magica on Duckduckgo. There are also Abrowser plugins Unplug and FlashVideoReplacer. Afaik, installing all of those will max out the amount of flash videos that work. If something doesn't work with the above plugins and/or Linterna Magica, you can only try searching for the respective video on some other platform like youtube, vimeo, etc.

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