Dropped $110 on a custom insert for Gloomhaven and my group quit the campaign 3 sessions later
I measured every single box and tile before ordering it, and the thing took 5 weeks to show up from a shop in Portland. The foam fit great, setup went from 20 minutes to 6, everything had a spot, and I was honestly proud of it. Then two of my four players moved away in June and the campaign just died on the table. Half of me says organizers are worth every penny for a heavy game you play weekly, and the other half says gaming money should go to new games because campaigns always fall apart. Where do you draw the line on organizing gear for games that might never finish?
My buddy Pete bought a big wooden insert for Twilight Imperium, like $150 with shipping from some guy in Poland. He spent a whole weekend gluing it together and sealing it with this oil finish. Two months later his wife got a job in Denver and the whole group fell apart. He still has that box on his shelf and every time I go over he points at it and goes "best money I ever wasted." But here is the thing, he says it with a smile. For him the fun was the building part too, not just the playing. If the organizing itself makes you happy then it counts as part of the hobby, not just prep work.