Again, you're thinking inside the box. You're thinking that Hawaii is a much better deal than Detroit, always. I'm saying technology can change the balance.
No, it can't. Technology can't change the climate so that it's balmy and warm all year round in Detroit. At least not without Kardishev Type II civilization-level technology (Dyson spheres), or perhaps The Matrix (which isn't physical reality at all). We're not talking about that, we're talking about, at best, Star Trek-level technology (Star Trek depicts a Type I civilization). Even Star Trek, with warp drives and phasers and replicators and transporters, does not show technology capable of turning the whole planet into Hawaii. In fact, Star Trek has many, many episodes showing human settlers on colony planets, because apparently there's too many people for the planets they have, and they don't have the technology to build Dyson spheres, so they send ships full of colonists out to empty planets to settle them. They even invented the Genesis Device to try to make more usable planets for colonization, but even that was limited in its capabilities (it could basically take an existing planet or collection of matter and turn it into an Earth-like planet, complete with different biomes, some probably really nice like Fiji and Hawaii, and others kinda shitty like Antarctica, Saudi Arabia, and North Dakota). And honestly, the Genesis Device really stretched suspension of disbelief even for Star Trek physics; the amount of energy needed to pull of such a feat would be enormous, and they didn't show how this device supposedly got enough energy to do such a thing, especially since it was only the size of a photon torpedo, and even those don't have that much energy in them.
Or he could just be Patrick Stewart (who did in fact dated the then-20 something Lisa Dillon for a time)
There's always a few women attracted to older men, but Patrick Stewart was a famous (and presumably rich) actor, and also unusually attractive for a bald man (or even any man for that matter). If he wasn't so attractive, and neither rich nor famous, and his goal was to bang young chicks, he wouldn't have had much success at that, unless he settled for some very unattractive ones. Lack of money isn't going to change this. Genetic engineering and various medical treatments could though. I only brought this up because of your quote about people in the 24th century supposedly not caring about baldness, which I think is bullshit. Lack of scarcity of most resources would change many things, but certain facets of human nature will never change unless we change ourselves so that we're no longer human. Lack of scarcity isn't going to make us all not care about physical beauty, or not be attracted or unattracted to other people based on physical appearance.