Getting custom silicon in older processes (>150nm, but even 90nm has come down dramatically and that's a pretty modern process) just isn't that expensive anymore. It's under $50K, and can be under $5K if you catch a "shuttle" that one of the fabs runs.
The VLSI CAD tools, however, are ferociously expensive. Even the old Tanner tools are now being flogged by Mentor for north of $100K. And they're probably the cheapest around.
We're not even talking heavy digital--old 2um or 5um (especially metal gate since they have 18V voltage tolerance) processes are interesting for analog audio. Guitar pedals still use analog bucket brigade delay chips that haven't been manufactured for decades. At $5K, you could make your money back on a boutique pedal if you sell 100 of them. At $50K that gets dicey and at $250K that will probably never happen.
The ability to slap a couple hundred transistors down on a chip, simulate it and get it manufactured for less than $5K would enable a lot of interesting, low-volume stuff--look at what happened when PCBs got so cheap.
Right now, the entire electronics industry is constrained by the fact that volumes are "millions or bust".