Haha this would make a good video, but yeah, I can give some insight.
The main reason I sold the Helios is because the ergonomics were poor. I also never really liked using the DX300 (I might have mentioned this before, but the main reason why I even purchased it was so that I could appear more 'official' as a reviewer). Eventually I just stopped caring what people thought, and I have plenty of dongles which are more convenient, so off it went. The bottom line is that comfort and convenience will always supersede sound quality in the long-run unless someone considers themself a masochist. So that's probably the first consideration I make whenever making a purchase these days.
To answer your other question, I wouldn't sell the Diva even if it wasn't a CIEM, although sometimes I wish I purchased the UIEM instead (as it's a PIA cleaning CIEMs). It's one of my main IEMs, as it compliments the U4s in a lot of respects (specifically in the opposite approach to the upper-midrange). And a major purchase consideration I had was that the Diva would be future-proofed for at least the next several years. The way it is tuned is very difficult to replicate (specifically the unique bass rise and the mid-treble tuning). There's still nothing on the market that sounds like it or offers that type of tuning flexibility in a single package.
Along those lines, I look for products that 1) sound unique and 2) that are executed tastefully. The reality is that IEMs with 'conventional' tuning have been refined to a very high degree already and they appeal to a common denominator, one-size-fits-all audience. There are some outliers that are on another level (think the Subtonic Storm), but I don't really subscribe to the idea of a one-and-done IEM, which the Storm would have to be for most listeners given its cost.
I can only speak for myself, but I know that I enjoy a myriad of different sound signatures. It doesn't make sense for me to sink all my money into one IEM. Hence why I've diversified my collection with IEMs like the U4s and Diva which also offer variability via the Apex modules or the bass dial respectively. Add in the Supernova and these IEMs cover 80-90% of my listening needs. I don't really have any plans to buy any IEMs in the near future; if I were to remotely consider purchasing something, it would not only have to offer something unique, but it would also have to be a good value.
To your last question, I'm not sure if I have any particularly spicy takes, but I'll point out that hobbies like audio are low-hanging fruit for flexing wealth and they promote echo chambers. This leads to many people feeling compelled to fit in by purchasing what others are purchasing or by sharing the same impressions. All this to say that I will often read impressions from others that I strongly disagree with. But when there's a consistency between their impressions, I can begrudgingly attribute it to a difference of taste. And I think therein lies the distinction: it's better to have trash taste than it is to not have taste at all and just parrot others' opinions.
Plenty of people have trashed my taste. But these days, it's difficult for me to bother responding to those types of comments (you'll see that I used to try explaining myself; now I just slap back or make a joke out of it if I even respond haha). I have better things to do in this hobby like going to events/meetups, traveling, and hanging out with my audio buddies. Basically, stop caring so much about the gear and what others think, and you'll have more time to focus on experiences instead which will make you happier in the long run.
Hey, no, I haven't heard it yet!