I would say the $300 the seller wants is fair, but I would offer $200 and see if you can meet in the middle for $250. That would be a fair price for this to make a nice conversation piece in your living room or man cave.
Your safe is not from 1940 like the seller suggests, here is some good info on the years Cary safe was in business and when reseller Featherstone was in business
http://en.allexperts.com/q/Antique-Safe ... afe-87.htm That puts your safe in more of the 1906-1915 range.
Driving to Quebec from Ontario to pick it up is probably your best bet, paying to ship it would probably add a few more hundred to the price, but then again, you have to pay for gas if you drive to pick it up.
It may be best to look for something locally in your area.
I saw a nice little safe in Florida on ebay and the price is right, but no way am I paying to ship it and I'm not driving 1000 miles either, just gonna have to pass it up.
