Hey nonnie! What a challenging ask! You posed many questions but they’re very interesting. I’ll do my best to do them justice and I hope I have the chance to read the answers from the other people you’ve asked.
1. Why do you think the chance of canon Destiel will happen and when?
I might sound delusional, but the narrative of the show (since season 8) and how they’ve been using the love tropes has gotten to a point where they can hardly go back. Even casual viewers have noticed the subtext, just because in some cases it’s been THAT obvious (the crypt scene still being #1). I know many people have lost faith and think canon Destiel won’t happen, but I remain confident. I don’t know, however, when it will happen. The only thing I can do is try to predict. I can give you my reasonable prediction and my shipper one. You choose which one you prefer.
My shipper prediction is that the perfect moment to make Destiel canon is the season finale that’s coming up. Why? Because everything makes perfect sense. The song that opened the season asked a very important question, “Who do you love?” The only character that has given us material to try to answer that question is Dean. In 9x02, Dean told Gadreel (Zeke at the time), “I’m not really with the whole, uh, love, and… love.” In 9x08 we got this from Dean, “Sex has always felt — I don’t know — good, you know? I mean, really, really good. Uh…But, uh… Sometimes, it just makes you feel bad, you know? You’re drunk. You shack up. Then, it’s the whole morning thing. You know, ‘Hey, that was fun.’ And then, ‘adios,’ you know? Always the ‘adios’.” That’s pure text. What about subtext? Gosh… where to begin? In 9x03, we saw a desperate Dean trying to find Cas. We heard his voice break when he thought Cas was dead and we saw him tell him angrily “Never do that again!” (Another love trope, btw). We also saw how Dean was forced to send Cas away in order to keep Sam alive. That was really hard for him as he reminded us in 9x04 (“Nobody wants [Cas] here more than I do”). Then we saw Dean go after Cas in 9x06. He went to Rexford, Idaho because of the case Cas called him about. True! BUT… Dean went looking for Cas and kept trying to get Cas’ help. In that episode, we even got that romantic scene where Cas is at the Gas’n’Sip and Dean is just watching him from far (similar to what Cas did in 6x20). Either we saw Dean smiling at Cas in a way only Cas can make him smile or we saw him looking at Cas with that sad face on when Cas was not looking. That episode can’t get more romantic than that! We even got the fanfiction gap and ‘always the adios’. In 9x07 we learned that Dean chose Sam over Robin when he was a teenager. If I remember correctly, Dean chose Sam over Cas in 9x03. Wait, who was Robin again? Ahhhh yes… Dean’s LOVE INTEREST! In 9x09, we get a montage for the mid-season finale that besides giving the audience bits and pieces about the season, it also emphasizes Dean’s prayer to Cas in 9x01 (just in case people had forgotten) and how Dean said there, “Please man, I need you here” (which Cas never heard, btw, but WE DID, and that’s important because IN CANON when Dean prays to Cas, he tells him that he needs him). In 9x09, we also get a blatant break-up between Dean and Cas. This is how the SupernaturalWiki transcript describes that scene:
(clears throat) I, um, I noticed you look… kind of uncomfortable whenever Sam mentions my leaving. Doesn’t he know that you told me to leave?
Here’s the deal. When Sam was doing the trials to seal up Hell, it messed him up. Okay? The third one nearly killed him. If I’d let him finish, it would have. He’s still messed up, bad.
You said the angel, Ezekiel, helped heal him.
DEAN (looks down, avoiding the question)
Look, I got to do anything I can to get him back. Now, if that means that we keep our distance from you for a little while, then… Then I don’t have a choice. I don’t feel good about it, but I don’t have a choice. It’s great to have your help, Cas. Okay, but we just can’t work together.
CAS looks sad.
Can you tell me why destiny or whatever other crap is going to keep two friends apart? There’s a trope for that (star-crossed lovers, destined to be kept apart no matter how hard they struggle to be together). And yes! As the name indicates, that’s a trope ONLY for romantic love. It’s not used for FRIENDS. Interesting, huh?
In 9x10 and 9x11, we got so much subtext that I’d better just link you to what I’ve previously said about those episodes here and here. But I’m just going to say that Cas forgiving and supporting Dean, and then the Cain-Colette story, the “I know you watch over me still” line Cain said while PRAYING to Colette… all that can’t be a coincidence! It’s subtext but… hey, Robbie Thomson (Metatron) said in 9x18 that subtext is one of the things that can make a story work!
In 9x12, we got more input from Dean’s mind regarding love. This is what he told Garth, “Well, hey, you said it — you know, who cares where happiness comes from? Look, we’re all a little weird, we’re all a little wacky — some more than others — but…if it works, it works. You got something here. Okay? Even though they are werewolves. Or Lycanthropes — whatever. Don’t let that go. Okay? You’ll never forgive yourself.” Dean-kill-all-monsters-Winchester said that it’s ok to love someone even if that someone is NOT human. He didn’t think that way when he killed Amy in 7x03. This is character development, thank you very much!
In 9x13 we got Dean realizing that one can love a person even if that person is not one’s type. And we got the interesting line, “The best of both worlds — salty and sweet,” which of course is open for interpretation.
In 9x18, we got an overly-concerned Dean. He called and texted Cas and worried a lot when he didn’t call or text back. He even turned on the GPS on Cas’ phone after 6 missed calls! And don’t even get me started on the little smile Dean had on his face just by listening to Cas being Cas. Dean has been worse than sad in the last episodes, and the only few times that he has smiled, like really smiled, has been because of Cas.
The parallels, the way the story is being told, everything makes sense. We’re heading to a moment when Dean will lose control due to the MoC, and who is going to be the one to open a window for him? In Cain’s case, only Colette, a person he loved, could stop his dark side. In Dean’s case, only a person he loves will be able to stop his dark side? The question is WHO DO YOU LOVE, DEAN WINCHESTER, WHO THE HELL DO YOU LOVE? Geez!! I have no clue! *sarcasm* Maybe Lisa will come back! *yeah right*
Now, my reasonable prediction is that Destiel will be canon till the series ends. They might continue toying with the idea, leading us to hope and believe but won’t do anything explicit because they will wait till the last second. Why do I say that? Because Dean and Cas are endgame and NO ONE will change my mind about it. Dean and Cas are going to be together at the end of the series even if Destiel is never canon, simply because they belong together. I just hope the show is brave enough to make it canon, because if they just pull some kind of ambiguous crap that will be open for interpretation, it will be the most disappointing thing in the history of television. (Sorry for the exaggeration!).
2. How far will they show canon Destiel i.e. touching, kissing, sex, dialogue? Do you think the actors will be comfortable with it?
It’s the CW… they won’t go that far! Sex… I don’t think that’s happening. I keep my fingers crossed for a kiss, but even that is a huge MAYBE. They showed us a same-sex kiss in 8x11 (Charlie and Gilda), but for some stupid reason it’s easier to show a woman-woman kiss on television than to show a man-man kiss. Canon Destiel will probably be just dialogue, but don’t expect a lengthy love confession, a heart-to-heart talk, or some cuddling or holding hands. That’s not what the show is about! And most importantly, that would be totally OOC for Dean and Cas. Don’t expect a speech about Dean coming to terms with his bisexuality. He will probably never even know. He will just think that it’s an exception. Period. ‘Who cares where happiness come from?’, ‘You can love someone who is not your type’, RIGHT? Two manly-men who happened to be hunters fell in love (8x23), why can’t Dean love an angel that, by the way, is genderless? Anyway, regarding the actors, I definitely think they would be OK with it. Most people worry about Jensen, but I have to remind you all that he has already played a bisexual character. He’s a professional and a great actor. He doesn’t like to talk about Destiel because… it’s creepy mostly if you see fan art or photo shopped pics, but that doesn’t mean he would be against it. In case you haven’t noticed, the acting choices Misha and Jensen have made for a very long time are what gave life to Destiel. There are many acting choices that Jensen’s made that we can analyze and write huge meta about. Jensen knows Dean Winchester better than anybody else, and his choices demonstrate that every time.
3. Will it be a good investment for SPN/CW for canon Destiel or bad? In your honest opinion what are the pros/cons?
Supernatural has been a very bold show since they killed Dean in season 3. They killed one of the ONLY two leads! Sometimes they’re not afraid of taking risks, that’s why I still think Destiel will be canon. Will it be bad? I don’t think so. Nobody can deny that season 9 has been very good in terms of ratings. And what episodes have the highest ratings? The ones where Cas shows up (or Misha directs). After the abundant subtext of season 8, many people started to have hope for canon Destiel. And they’re still watching. Many people started watching in season 9 (and probably watched the previous seasons on Netflix because they heard about Destiel… I know many of those people). Do you have any idea how much media attention canon Destiel will bring to the show? A show going into its 10th season needs something fresh. The constant angst between the brothers… that’s definitely not fresh and it gets boring and overwhelming after the hundredth time you see it. The pros of canon Destiel if they do it right: a lot of media attention, MANY new viewers for season 10, huge support from the part of the fandom that wants Destiel or is simply OK with it. The cons: some people will stop watching the show, but I don’t think the number will be big enough to worry (compared to the new viewers). I even think that the ratings will remain very similar to the ones obtained in season 9 for Cas’ episodes. Some other cons: haters will spread even more hate (noooo… really?), and the hard-core “just the brothers” fans will go ballistic! (About that… I don’t care that I don’t care!).
4. Why are we seeing more Destiel contents in the media, actors twitting bout it? And Robbie with his Pro Cas tweets?
Honestly, nonnie… They are being smart! I mean actors and Robbie, and anyone who tweets about Destiel in a positive way. You saw what happened last year to the poor guy whose name I don’t even remember? The executive producer or something? Poor guy! The actors and writers know very well what Destiel means to the fandom (and noooo… we are NOT the 1% of the fandom. It’s amazing how many shippers go to Cons, you know? But many try not to say they are shippers until they know you are a shipper too because they’re just afraid of being bullied or something). The choices writers, actors, and directors make show very clearly that they toy with the concept of Destiel a lot. Even the music they choose toys with the concept of Destiel sometimes! And regarding Destiel contents in the media… I guess you’re talking about some very nice articles that have been written. I think it’s because the show has pushed the subtext and the love tropes so much that it’s starting to be ridiculous. Some people think that it’s not a matter of IF anymore but a matter of WHEN Destiel will be canon. Only time will tell if they are right. Robbie’s Pro Cas tweets? Well, I think that everybody who is active in social media knows that Misha Collins is a VERY important factor for the ever-growing popularity of the show, not just because Misha is very well loved, but also because Cas is the favorite character of MANY MANY people (as the ratings can prove). I’m sorry for the people who would like to go back to the first 3 seasons where Cas was not around, the truth is that Cas is a huge part of the show whether they like it or not. They will make us suffer in the season finale, the cliffhanger may or may not have to do with Cas surviving, but I don’t have a doubt in my mind that Misha/Cas will be back for season 10. It’s simple logic and business.
And… holy mother of Chuck, I finally finished answering your questions. It took me long enough! I hope my answers are somewhat what you were looking for.