I’m focused on NES, SNES, N64, Master System, and Genesis at the moment. I’ve just about reached the end of the cheap NES games and bought an Everdrive N8 Pro earlier this year. Mainly for ROM translations and homebrew, but I will admit to playing some of the higher dollar games on it. I’d much rather play actual carts though.
For me personally, I’ve found that I’ll go upwards of $60+ for a RPG or meatier action adventure game, but haven’t so far spent more than that on any of the consoles.
I’ve also opted to buy ports over original games in some cases. Chrono Trigger for example, I won’t spend $250 on it so I bought the Japanese DS port since it was $30 shipped and supports English out of the box.
PAL/R4 PS1/2/3 & PSP collector here; there’s no hard & fast cut-off rule.
But I would need to have a deep and personal connection to the title, and it would need to meet a number of requirements (case type, game variant, CIB, disc scratches etc.).
Even then, I’m still going to struggle to part with >$1,000 dollarydoos for Castlevania: Symphony of the Night Special Edition!