That's an unethical and impotent strategy. Simply owning a domain without using it is not squatting. Having a trademark does not give you rights to someone else's property either. See Nissan Motors vs. Nissan.com.

The UDRP only allows you to take a domain for trademark infringement if:

a) the domain name is identical or confusingly similar to a trademark or service mark in which the complainant has rights; and

b) he/she has no rights or legitimate interests in respect of the domain name; and

c) the domain name has been registered and is being used in bad faith

The squatter has several names registered, has indicated to me that my particular name of interest is for sale, and he asked me to give him the best possible price. I said $300, and I never heard back from him. If I want to use the name, do you have any suggestions?

    I said $300, and I never heard back from him.
    If I want to use the name, do you have any suggestions?

Bid more than $300?

If you don't know how much the domain is worth, you should do some homework. Here are a couple of sites I've used when attempting to determine the market value of a domain:

http://www.domaintools.com/buy/sales-history/

http://www.domain-prices.com/search/prices/5000

I have tried those services. They never give me any info - you see, nobody has ever used that name before.

Is there a way to see how long he has owned the domain? From there, estimate a yearly cost to him (12$ * years registered) + 10% profit and start from there. That seems reasonable.

You can use whois to see when the domain was registered. Since all the other extensions weren't registered I'd assume this is more of a brand style name and was registered fairly recently. It is hard to assign value of a domain without knowing what it is. Also, most people who sell domains are looking for the sales to compensate for the rest of their portfolio that don't sell. So registration fees + 10% wouldn't likely work as an offer.

The economics of owning a lot of domains pays off when your portfolio covers the cost of all registrations/renewals. The average churn rate on big portfolios is 2-3%. So simply offering a 10% on top as profit doesn't work. The average sale price is ~$2000.

If he owns the domain before you setup your business and do the trademarks he can keep the domain. Your logic is very flawed because you don't understand the process.

If I were you I wouldn't use a non-geographically neutral extension to start with, unless you only intended to keep your business strictly in Canada.

Really tired of people calling legitimate domain investors "squatters"

I'm tired of domain investors being called legitimate. It's free and open space; take what you need and leave the rest.

... You're probably the person before the hurricane who buys all the gas in the neighborhood and resells it to people for 1,000 times the price.

Or invests in a company that looks like it might hit it big before everyone else does.

I agree whole heartedly with this statement. To all "domain investors": Please tell me how you add value to the human race by investing in domains?

It's what Groupon did, but I wouldn't recommend it.