Can I... (trademark question)

There is no hard and fast rule except that trademarks are protected (i.e., brands are protected).

Nothing to stop you from registering the domains...but the company holding the trademark may come after you if you try to use the domain. So often marketers are excited to find a "brand name" domain 'available' - not understanding the reason for availability is trademark protection. No sense in registering a domain that may result in a cease and desist letter the moment you launch a website.

It's possible you can get by with it - and just as possible you can't. It's possible a court would decide in your favor - and just as possible it might decide against you. If you are selling food on a domain using a trademark registered for "pies" (which is 'food') - not a good risk to take in my opinion.

They don't have to pay for all domains - the Trademark Registration protects their company from other people using the name/domains.

Most of us stay away from trademarks - because the potential problems aren't worth it.

You can do it until the person complains or makes a big deal (that doesn't mean you should), small companies will often not do anything, really it's up to you if you want to take the risk.

Rule #1, when in doubt, forget it.

Have they actually registered the trademark? What is the trademark on? Is it specific to pies? is it just for the logo? Is it related to all foods?

Check these things out by all means, but the chances are they could have you shut down if you try this, so I would think of a different name...

If you want to start a business you want to create your own unique branding. You want to differentiate yourself from everyone else in the marketplace. Your domain name is the home of your business. Imagine your friends were constantly going to your neighbor's house because they thought it was yours. That would be annoying. If your domain name is too similar to another business you could inadvertantly be directing traffic to your competitor especially if they own a .com. This would also be confusing to your customers. You want to also make sure that your chosen name is available across all social media platforms. Again, this is important for branding purposes. I recommend you run a name search here:
https://www.namecheckr.com/
It's free and you can see at a glance if your name is available across many social networks. Hope that helps.

Another smart approach would be to see if you can license the name from the trademark owner. If their site is as dead as you say, they may be happy to get some cash flow where there is none now.

Of course you can, this is why businesses buy more than one domain name to protect from others doing just that. If they haven't bought the .ca version then they should have. There is no automatic ownership.

The only thing you must consider is that while you are working to try and market your own brand and drive traffic to your site you will of course be doing so inadvertently for them. And you may argue the same goes in reverse however if they are already a well known brand people will search for them click on you and then realise you are not them and leave your page, so you may endure a high bounce rate, which will affect your Google ranking.

So, I would personally look to rebrand, buy the extra domain names and offer to sell them to the company and make some money

Thanks guys, some good ideas, I think I'll go with creating a brand for this one.