I've held an Advanced ticket for 48 of my 50 years as a ham, and have never seen a real need to upgrade to Extra. The only differences are getting the bottom 25 kHz for CW on 80, 40, 20, and 15, an extra 100 kHz on 80 plus 25 kHz each on 20 and 15, and a usually-unobtanium 1x2 or 2x1 vanity callsign.
I haven't had a CW QSO in about 30 years, and I don't really miss the Extra phone bands. Then, getting any kind of vanity Extra call is like wanting a rent-controlled apartment in Manhattan: You usually have to wait for someone to die.
I use digital modes for most of my operating, and only run SSB during contests. No Extra license required. If I ever change my mind, it'll be because I just want it for the heck of it. Changing my call from a 2x2 starting with W to another one starting with A is a non-factor.