Sounds like you are in the very early stages of your surf journey. Only advice I would give is make it a personal journey, think less of what others are doing and focus more on yourself. By that I mean grow your surfing where you want and focus less on feeling salty about dudes riding "expensive" boards.Something I am wondering, as I read all these replies/recommendations, is how much of a real difference there is between all these shapers and boards? Is it all just placebo and what a particular buyer thinks he/she is getting? I don't mean in any way to belittle the craftsmanship of these shapers, I've been looking at the sites of all the shapers recommended and their boards are gorgeous and their passion for their craft is apparent, no doubting that, so yes there is a difference between cheap boards imported and someone who has the skill and hand shapes (or has a team that handshapes) boards ... as far as quality goes. But, at what point is there really no discernable difference in how a board helps "you" and what the real difference maker is, which is your own ability?
Is Michael Jordan still the best basketball player if he was wearing Walmart sneakers instead of Nikes? Does Kelly Slater still outperform 99.9% of all surfers if he's on a Wavestorm? Just like a placebo in clinical studies, do you just think a board performs better because you ordered it custom and waited 6 months? And if it is truly better, what is the actual gain ... catching a wave half a foot earlier? Turning slightly faster? Isn't it really your skill, fitness, and ability that makes the most difference.
I've seen surfers locally rip on beat-up and duct-taped Bics, Wavestorms, and other "lesser-quality" boards because they have the skill, while others flop about, hardly catching anything on custom-made Ricky Carrols, Jim Phillips, etc. ... and some of these folks I've talked to in that latter group have been surfing for years, if not decades and they're just bad surfers, or really out of shape, but swear by what these boards can do for them, which from what I can see ... ain't much. It's like we're into different realities.
Another example is me. I am only into this sport about a year. I am newb/kook, but I am an exceptionally strong swimmer, so I can paddle with some pretty decent speed and catch waves earlier and faster than most. Once I get up, it's a different story. Some days I go out and mentally I just feel like I am going to have a kick-butt session ... and I do, relatively speaking ... other days I am just dragging, and using the same board, with even similar conditions, that's what happens. Even within a session, I see big variability ... some waves I am relaxed, my mind is clear, I am ready for and have a great ride, while other waves, which may be very similar, I am just not in the zone for, and have a crap ride.
I like the boards I am seeing from all these recommendations, I honestly do, and I've reached out to some because I am genuinely interested, but I don't think they make that much of a difference. I think in general, there are clearly different style boards for different conditions and how you want to surf (though these groupings are probably rather small ... Longboards, Funboards, Shortboards), but the real difference-maker is your own ability. Maybe it's 80/20, 80% ability 20% board ... but maybe it's even skewed more ... 90/10 or even 95/5 as I think about those surfers who tear it up on Wavestorms and duct-taped Bics ...
Is it worth waiting 6 months+ for a board? If it's to support the "local" shaper and because you like the look/feel of their board(s), have the disposable income, want something that's personal and arguably a work of art, and have the time to wait, then probably yes, it's a hobby, hobbies can be expensive, they're cultivated over time, they bring about enjoyment and happiness when viewed in that lens. Going back to Jordan, Slater and others at the top ... when you're competing at that level, where you're dealing in such tight margins with other highly skilled competitors, the equipment can indeed help ... but for the vast majority of us, I don't think it matters all that much and we just need to become better surfers.
Just some random thoughts...
Sounds like you come from a competitive background since most of the examples you bring up focus on outside perception of performance. That is certainly one approach, however you also need to factor in the enjoyment aspect and chasing a feeling.