Avoiding rambling mostly off topic on another person's post, so I'll just spill it all over here instead.
Sam had a tv from pretty much the moment they moved into the bunker. We see it in Pac-Man Fever when they all gather in Sam's room to watch Game of Thrones. In s11 during Cas' recovery period Sam gets him hooked on Netflix.
Which is actually fascinating in and of itself. For years Sam was the one with a tv. Just Sam. Not Dean, the tv and movie reference guy. And once Dean gets a tv, it's in a group space. Even when he's watching something on his laptop he does it in the library.
The only time we ever see Dean watch something in his room is in Mint Condition when he's full on depression caving (and presumably took the TV from the Dean cave) and hiding from the AW!hunters. Outside of that one instance he'll read or listen to music in his room, but he doesn't watch TV or movies.
And we don't know when exactly the Dean cave was created. Just that Sam didn't learn about it until s13, long after it had clearly been finished and in use. So why did Dean put it together? We've been shown that he's okay with watching on his laptop in the library. He clearly wants a separation between his own personal living area and the tv/entertainment area.
(Presumably because motel rooms are set up with tvs right at the end of the bed and he's not living in a motel anymore.)
But, Cas loves TV as much as Dean does and with as little discrimination about the exact programming. We've seen Cas happily watch infomercials and know he enjoys trashy talk shows. Outside of the beginning of s11 Cas just doesn't spend a lot of time at the bunker. He spends most of s9 and s10 doing his own thing/supervising Sam's secret project. S11 he was posseased by Lucifer and then kidnapped by Amara for the vast majority.
So, S12 is when he really starts staying for longer periods of time. S12 is when Dean is looking at potentially weeks of Cas hanging around and sitting in the library in the middle of the night is no longer appealing. S12 is the most likely option for building the Dean cave and the most likely reason is a comfortable place to hang out with just Cas. No Sam wandering in during the middle of a movie. No one complaining that sound travels pretty well from the library and asking them to keep it down.
The Dean cave was built to spend time with Cas. The only reason Sam ever found out about it is because of the circumstances of the eventual TV acquisition. The place was fully constructed and in use by the time Sam sees it. And there is no way Dean got all of that set up by himself, Cas had to have helped.
But the Dean Cave was used as a place to hang out with Cas. Yes, movies and TV shows on the laptop, probably on a table pulled up inbetween the recliners. But also Dean and Cas sharing a drink from the bar, playing fooseball, listening to music, maybe sitting silently reading together. It's the first place Cas goes to look for Dean. They spend time there.
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