The "audiophile" dilemma-- buying records that make your system sound good, or because you like the music? Granted, some records are great music and great recordings, but part of that depends on your taste, your pocketbook and where you are in accumulating LPs.
I eventually found the "sonic spectacular" stuff to be a dead-end; musically, just not interesting to me and I'll include within that, lots of soft jazz, classic rock warhorses, etc.
I know Mike likes the Classic 45s. I have two of the 45s- I didn't buy the road case when it came out. On LZ 1, I actually prefer an early Japanese pressing, but that may be subjective and based on system. I find a lot of audiophile reissues emphasize detail and have a somewhat 'tipped up' top end.
If you are buying for sonic spectacularity, there are endless resources on the audiophile fora. Much of this stuff gets reissued repeatedly because it is a safe bet for sales--
I've fallen into the trap just like others- in some cases over a dozen pressings of a particular album.
I think it is a journey of exploration for me at this point in my life. I'm interested in more different music. As one example, Cochemea Gastelum's All My Relations on the Daptone label is a mix of Native American chants, electric sax, BIG drum sounds and is a cool listen. It will set you back 20 bucks. There's all kinds of deep jazz- not necessarily straight ahead, but a little more challenging- that you can find for almost nothing if you are willing to explore-- but that may not be your thing. Classical- the market is dead, except for a handful of high value records and there's a lot of good stuff if you know what you are after.
Since it sounds like you are just building a collection, I would start with music you like and then research what the best pressings are; the Steve Hoffman forum is good for classic rock. If you are going to buy older records, you'll need to educate yourself. There is consensus on the audiophile favs but most of it is stuff that I don't listen to at this point- not b/c I'm a snob, but because it doesn't do anything for me. In other cases, it goes back to what you are after- AJA, to my ears, is a very dry sounding record; the Cisco, which everyone raved about is even more antiseptic sounding. Some people think this is great. Who am I to say. It's not my cuppa. (the AB press sounds better, standard issue stuff if you like that record).
I actually managed to avoid listening to Dreaming with Dean or whatever it is called for a year or more, but got caught out one afternoon when invited to hear a very fancy system and the moment the needle came down, I knew what it was. Kinda broke my avoidance streak on that one.
You'll also wind up playing in collector territory if you go deep enough. They aren't audiophiles. These are blue chip artifacts collected by geeks in band T shirts that are two sizes too small. Who knows if they'll be worth the kind of money they are currently fetching in some cases. I've spent serious money on some records... because I liked the music. Buying records is generally not a good investment, ,but if you are starting out, I understand why you want to be blown away. Just keep in mind that at some point, you may feel like you've been eating at an amusement park and there is far better fare elsewhere if you care to look. Hell, if you ate at 3 star Mich restaurants in France for a couple weeks, you'd get sick of it too. So, while you build your collection, read, listen, research, and surf artists. There's a ton to learn, and that's where a lot of the fun is, for me, anyway.