I think we do think similar....too similar. I too wish to own a nice Les Paul one day ( well, two, preferably one normal and one custom made with 7 strings and chambering). And I also wish every guitar of mine, with every switch position to have a own flavour.
Also your kid analogy is nice. But I feel like I need to get a kid to be able to handle its own before I get a new one. I only move on to new guitars if I am satisfied with the way the old ones are. Might be me, but when I think like: " Hey my Ibbie doesn´t sound good....oohhh there´s a semihollow telecaster with P90s..." I first switch the Ibbie pubs, because of my relationship with it and because it might just lay around after buying the new axe, cause I don´t feel it has any use (same reason I don´t want 2 guitars sounding alike).
Plus I so far always after switching PUs felt like I had a new guitar alltogether, like a kid jumping from infant to graduate (not in a sentimental, in a good way), where you wonder how that could have once been the same person.
If you feel ok with what you have go for a new guitar and sort out which that might be.
If you´re not comfortable with what you have, feel like you don´t like to play one of your axes, have it just sitting around cause it sounds bad, but somehow still love it, concider upgrading that one. It could be like teaching your kid how to ride a bike.
Play what you have, really listen and then listen to what your heart says.
Again, my view only.
Btw, your way might have been more extreme, but still I think that this thing in red
http://www.ibanez.com/ElectricGuitars/model-S570B does not exactly scream "classic rock" at you.