Thanks, I think you're totally right about bittersweet being a good thing. I've done a few "there's always something"s myself, and you're right the most important thing is that it doesn't feel like a setup. Which I think is actually mainly what's been bothering me about this: it's the fact that I feel like he was reaching for that point in the first place and then John says he's wrong and it's like... okay, whatever. So actually fixing the reasons and the setup for it has fixed my issue almost entirely - and a detail I found while doing that has given the bittersweet a little twist that fixed it the rest of the way. So thanks, you've been very helpful!

Yeah, I'm generally fixed in a close POV - this is most likely all from John's POV - but I need to make an emotional connection with a character before I can act as their puppeteer, even when they're not carrying the POV. They don't necessarily have much description--describing characters and oh god, naming them, is the hard bit for me, which is why this particular situation is making me wibble--but they can't even walk into a room until I can feel them from the inside. Actually, I've just thought of another story I was fighting with this problem and managed it quite well by basing each of the short-range OCs around a character from another tv show/movie that would be recognisable only to me. I should do that again.