If you're a visitor with an expired TRV, I don't think you would be able to apply inside Canada for the work permit. You would need to apply at your home Visa Office or Port of Entry (USA border). That is, unless you fit into one of these other situations as listed.http://www.cic.gc.ca/english/work/apply-who-eligible.asp
You can only apply for a work permit from inside Canada if:
•you have a valid study or work permit, or your spouse or parents have a study or work permit;
•you are a postgraduate from a program at a Canadian university, community college, CÉGEP or publicly funded trade/technical school (or other eligible school or institution);
•you have a temporary resident permit that is valid for six months or more; and
•you are in Canada because you have already applied for permanent residence from inside Canada. You will have to pass certain stages in the main application process before you can be eligible for a work permit.
It doesn't matter if you apply at the border or a Visa Office, it will be someone's decision to grant or deny your work permit. However, you're out of status - unless you've applied for an extension of your Visa before the old one expired. Because of this, you are considered a high risk to overstay - because you already have. I wouldn't be surprised if you're denied a work permit. (If you have an extension of your visitor status pending, then you can ignore this part.)
Maintain legal status is very important.