I have both the Timeless AE and Blessing 2 (but Dusk variant). I used to own the Timeless OG too, but sold it in favour of AE. In terms of fit, Timeless AE is a better fit compared to B2 to more people due to its smaller nozzle. I've let people try them, and more people complained about B2's fit.I am interested in the Timeless and have got some questions:
https://headphones.com/blogs/reviews/7hz-timeless-ae-review-a-year-of-difference
So the AE is different but not better? Is the fit better than the Blessing 2 for smaller or average ears? The B2 makes it difficult. 160 € for timeless, 210 € for timeless AE or 250 € for the Blessing 2. There are a lot of good iems here.
About sound quality, really depends on the priorities you're looking in audio. Timeless OG and AE are more resolving than B2. Between OG and AE, I'll go with AE as it has less treble edginess. I think the EQ that jasonb posted earlier is a good solution if you think the bass in AE is too much.