Ouch, that hurts to see.

A good carpenter could probably have that looking decent again for $500 or so.

Getting the machine back to "collector quality" will take thousands of dollars if you can find someone willing to do all of it.

Unfortunately, from my experience in shipping games (decades with dozens of companies) most LTL freight companies like Pilot will not insure for machine value and instead insure/pay out for damage based on weight. So for a pinball machine they will probably offer at most $500, unless third party insurance was purchased.

This is why I typically (for long distances, only) use STI. Yes, they are expensive, but they handle these games with a bit more care and value-based insurance is included. And yes I ship with the legs on all the time. I've posted about my process here plenty of times.

Of course the last part doesn't help you now OP, I'm sorry. I would push the freight company to pay out as much as possible. See where that goes, and decide from there. Good luck!