I really do not like lossless, for several reasons, the level of compression and manipulation done when mastering these is a bit of an unknown.
It is pretty well accepted that music producers will often create several versions from the original master recording for different market sectors. Often low res digital, especially for pop/rock market will have the low end frequencies boosted, reason being often it is listened to on headphones/earbuds, so this tries to overcome this. CD level files are usually good but compression can sneak into these as well, and dynamic range suffers greatly, there are a number of well known sound quality issues, known as the āThe Wall of Soundā. I think some Oasis albums suffered from this on vinyl and CD, and a load of other big artists.
Re-mastered or re-issued CDs and Vinyl is another can of worms in terms of SQ, often these are from digital copies of the āOriginal Masterā, whatever that means, probably a 2-track master copy taken at some point from the original multi-track master. So what ends up on CD and/or vinyl is completely at the mercy of the engineer and whether he/she tinkers with it or leaves alone, and if re-issued for digital streaming the same can be true. For example I have at least 5 versions of Led Zeppelin I from different periods in time, Vinyl, CD, digital files and all sound different, a couple are good, and one sounds very odd(compressed, dull and lifeless).
Unfortunately the music industry IMHO has dumbed down on SQ(sound quality) to support streaming to the masses. Probably 2 generations now know no difference and just accept it as it is. Basically in the early days file storage, and bandwidth was at a premium so making that package smaller meant it worked and was cheaper to implement.
Today even Spotify premium is questionable, it may or may not be at CD SQ levels(320kbps is not), it is well known that they will and do use lower res if their bandwidth and servers are at full chat. This is a good article on these issues High-Resolution Audio vs. CDs vs. MP3s as Sony see it
Having said that it can be very difficult to hear the difference between a very good 320Kbps digital version of a piece of music and the same at CD SQ(uncompressed).
Digital SQ is a huge and contentious topic, certainly at the end user end of the market.