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How easy would it be to add software so you could browse the dashcam USB stick natively?

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It's simply a matter of software.
But there are a couple of issues.
The first is that the browser doesn't have codecs in it, to watch video. And because of state laws banning drivers from seeing movies, that will be hard.

The next is that it is too easy to take out and view in phone or pc
 
It's simply a matter of software.
But there are a couple of issues.
The first is that the browser doesn't have codecs in it, to watch video. And because of state laws banning drivers from seeing movies, that will be hard.

The next is that it is too easy to take out and view in phone or pc
This would be a big issue but could be enabled when stopped.
 
Enabled video playback would be trivial... but for Tesla seemingly going out of their way to not allow any video on the display at all (see the browser not supporting any for example)

No reason they couldn't limit it to only working in park... but then they took like 6+ years to get USB playback to resume (supposedly finally fixed in latest build) so I wouldn't hold my breath