How long till there is a self-service SaaS for this?
An example list of steps: https://www.usjpc.com/en/ourbusiness/shuttle.php
the other is that the fab schedule is heavily laced with sales politics. getting a timely slot is largely a factor of how important a customer you are and none about scheduling work. they have as much work as they could ever want.
only exception to this is China. it's slightly easier to do this there at the moment. through they often transfer TSMC heavy-weights to manage their fabs.
Again, the market for this is tiny. How many companies do you really think want a shuttle service?
Either you're really big and can put serious resources into R&D and production, or you can have a few toy-sized offerings for the lowest end that are only good for highly custom or testing purposes, or you are too small to care.
Like what would drive the cost of a custom chip being cheaper than adapting something more of the shelf?
As for "can you order more if SiFive goes out of business": the detail here is going to be in all the other bits on the chip. Maybe they're free licensed, maybe they're not. You probably wouldn't get the GDSII that SiFive sent to the fab. You'd need to arrange another shuttle run. You might be too small for the fab to return your calls.
It's a pretty niche kind of manufacturing activity. Not many businesses really need a custom CPU.