Not sure how things specifically work in Canada, but there are some similarities with US law due to it all deriving from British common law (except for Louisiana, which bases everything on the Napoleonic code).

For one, the court considers not the value to buy new, but only the value to replace. This helps and harms depending on circumstances. Say you buy a new xbox game for $60 and I smash it. The court would only award you the average second-hand market value of maybe $40. Ah, but what if the item in question is a collector's item that's no longer in production? Doesn't matter how much you bought it for, it only matters how much it costs now to replace it. You can see how this is advantageous.

Like a classic car, the dollar amount in the suit will probably revolve around how much it costs to repair. Here in the states, reproduction parts are usually used as opposed to (much more expensive) OEM parts unless you can convince the judge otherwise. However, there isn't exactly a huge after-market for pinball parts compared to car parts. Especially when it comes to plastics and toys and artwork pieces that cannot be reproduced by multiple sellers without copyright infringement. This also works to your favor, because the shippers can't fall back on cheapo inferior copy-cat parts.

Here's what you should do if you haven't done it already. Take an inventory of every individual part that is broken or not working properly. For each one, look up how much it would cost to replace it from at minimum three reputable sellers (pinball life, pinbits, marco, bay area amusements, etc). You might not even be able to find more than one seller for some parts, in which case you might have no choice but to look at ended ebay sales. Get quotes from at least 3 reputable restorers on how much it would cost to do the repair (including building a new cabinet and adding decals).

My point here is that the shippers are going to take you to the mat claiming that you're just spouting off whatever inflated prices you can think of. The judge won't know anything about pinball or the pinball market, and they will take advantage of that. Your goal is to get all that pricing info to your lawyer so that he/she can make the judge see reality.

I would not be surprised if the lawyers are talking about "bailment", a legal concept which is found practically anyplace the English ever stepped foot. It's basically describes any contract wherein property changes possession but not ownership. These are things like borrowing your neighbors tools, paying for valet parking, and most importantly the transporting and delivering of parcels.

Because the agreement you initially entered into with the seller was to both of your benefits (you get your machine and they get money), they can't just absolve themselves of all liability with some fine print like it's written in magic ink. By default they take on liability called "duty of care"; they have the implied "duty" to take reasonable and normal "care" of your package in its transportation to you.

Duty of care is established by three things:

1 - reasonably foreseeable: It's easy to foresee a pinball machine getting bumped around in transportation, so you you took precautions to have it wrapped and well-padded with shipping blankets. Especially so since shippers all say they are not responsible for damage in the fine print.

2 - relationship of proximity between defendant and plaintiff: You contracted with the shipper to have them transport your machine in exchange for an agreed-upon amount of currency.

3 - it must be fair and just to impose liability: Given the precautions taken in 1, it is only fair for the shipper to do their part and be expected to deliver the machine with no damage or only superficial damage.

Don't know what Canada has that's equivalent, but in America I can take my itemized costs to the county clerk and have it registered as "verified debt" against the shipper of which I am a creditor. I can then report the debt as delinquent to the three credit reporting agencies here and hurt their credit score, or I could cut my losses and sell it to a debt collector.

I've done this twice, but in completely different circumstances. Both I sent to the credit reporting agencies. On one I sued for amount + double in small claims (Texas allows 3x damages for punitive reasons up to a max of $10,000 USD) and settled out of court for the amount + 40% punitive to cover semi-related fees. The other actually went to small-claims court. Defendent was a no-show, so I got a default judgement of $10,000 (just under triple damages). Sold the debt to a debt collector for the cost of my damages plus a little extra for fees.

I'm not a sue-happy guy, and Americans do get a reputation for such, but sometimes you just have no recourse when large dollar values are at stake and your dealing with a slime-ball. For some reason, transportation and repair services for heavy and expensive machinery seems to have a greater-than-average occurrence of dishonest characters.