First step, again, is to apply for an ESTA online. If that's granted, you're golden. If not, at least you KNOW you need to apply for a B2 visa. This will be harder to get than normal, but if you explain that you overstayed when you were very young, you have a higher chance. Not having a job is a pretty big downside, but if you can prove you have good reasons to return to Canada, you have a good chance. A visa will NOT cost over US$160 plus costs like transport and photos. Forget the lawyer for now. Also, the visa can be valid for up to 10 years if you're lucky, so this is not necessarily a yearly expenditure. It's possible that they'll give you one for a shorter period to see if you overstay again, though.