I'm legit conflicted, lol. I've always had the stance where I try to only upgrade my phone after I've had my current one for two-ish years. It typically doesn't seem worth it, to me, and while it wouldn't break the bank for me, it's probably in my best interest to not buy a new phone right now.
That said, the reason I'm conflicted is because of the trade in option. I have a Pixel XL, and I'd ideally like an XL 2. Assuming my phone gets full trade in credit, $410 off a Pixel XL 2 is very tempting. If the trade in option exists for the Pixel 3 next year, presumably my current OG Pixel will be worth significantly less for trade in than it is now. So, I could get $400-ish off a new $900-ish phone right now, or I could wait til next year and get $200 or less of a new $900 phone. I'd rather not spend that much money right now (especially because when the Pixel 3 comes out next year, the "new tech" bug will probably bite me again and have me question whether I should upgrade again anyway), but by waiting, I ultimately spend more money when I do upgrade later.
But, I'm also kind of conflicted about whether I even want to part with my current Pixel. Even when I upgrade, I kind of feel like my current Pixel would make for a great spare camera for stuff.
Sigh. I dunno.