> My two monitors are duplicating the
> display instead of extending as two separate displays.

Have you tried going to System -> Control Center -> Displays?

> Also: when it detects non-free software, is it always going to black screen?

No. Trisquel does not include proprietary software, but it does not impose 
restrictions on what you can install manually. I've seen installing the wrong 
graphics driver black screen Ubuntu upon startup as well.

> When booting
> in upstart, I saw recursively looping messages saying something like "Free
> Firmware Required".

Are you on Trisquel 7 on 8? Trisquel 8 should be using systemd, not upstart. 
When I was on Trisquel 7, I similarly got an endless stream of "free firmware 
not found" messages. The solution was to blacklist my computer's proprietary 
WiFi card.[1] In my case, the firmware was called iwl3945, which I got from the 
looping error message, so check the message (or post it here) to figure out 
what it is in your case. I had to do this every time I installed Trisquel 7, 
but it has not been an issue in Trisquel 8. 

[1] 
https://trisquel.info/en/forum/trisquel-not-detecting-thinkpenguin-wifi-adapter-after-install#comment-118182

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