I've had an interesting experience with old/vs new. I've been playing over 30 years, but new to TB as of a couple years.
BEFORE TB - I assumed everyone felt the same as me. I listened to a lot of "fresh string" type players - everyone from low slinging pick users like Duff McKagan and Krist Noveselic, to the older generation rockers like John Entwhistle and Chris Squire, to heavy harmonic users like Jaco Pastorious and Victor Wooten, to slappers like Larry Graham and Louis Johnson. Just as examples. I also read BP and other music trade journals - as well as advice from my private teachers. Seemed to me that most roundwound users liked fresh strings and changed them often - this goes for recording engineers too - I've heard of cats using fresh strings for each take in some instances.
Flatwound users seemed to be the opposite - James Jamerson, Joe Osborn, David Hood, Jerry Jemmott, Bob Babbitt, etc - these guys liked old flats, and were borderline superstitious about changing them. I once had a bass with 8 year old TIs - that were still going, but I sold the bass.
JOINED TB - Now I'm aware of a whole different spectrum of players. People who hate fresh roundwounds!! "I can't wait until they break in." BREAK IN?!? "This bass for sale includes a gig bag and a set of XYZ strings installed." Huh?!? The very first thing I always did when I bought a bass was change the strings! That's like selling a car "with Shell gas in the tank." I've seen cats on here selling basses with the factory strings - seemingly as a selling point. And now I'm aware of extreme users like Ben Sheppard - he only likes super old rounds - over 2 years old he finally starts to like them.
Don't get me wrong - I've always tried to get the most out of my roundwounds - but I always assumed I was pushing the limits by making them last 3 or 4 months. I did it because I'm cheap - certainly not because the broken in tone is desirable to me! I'd change them almost every gig if I could afford it.
Now with the flats - again I'm aware of a whole new type of player - guys who regularly change out their flats (talking like...2-4 time a year). I know of a lot of pro level players - off the cuff Tim Lefebvre, Michael League, Steve Harris, Carol Kaye, John Paul Jones when he still used the jazz bass.
It just goes to show, there's a time and a place for everything. I let the style of music I'm playing dictate the strings I'm using. I love old flats, and have a few basses dedicated to them, but recently I've needed fresh roundwound twang for some songs. I've also been using an octaver for synth type sounds, often with long held out notes - this dictates I use fresh rounds and heavy compression for maximum sustain, or risk tracking glitches. And it just goes to show how cool TB is - its opened up a whole new world! I mean, I used to own ONE BASS!!
Aloha! (if anyone is still reading this)