To me it appears you are more interested in coming to Canada than working or studying in itself. Nothing wrong with it per-say BUT if you apply for a study permit or work permit with those intentions then that runs counter to the conditions of those permits as you may appear as a non genuine temporary worker OR a non genuine student.
My wife is herself doing her masters here and she is repeating her masters BUT there is a very valid why she is doing that.
Now to answer your question, no, you should NOT join masters or diploma. It will only hurt your chances if you repeat your degree OR if you take a diploma that is lower than a masters. A Phd may make more sense but one should do a phd ONLY if one wants to be a researcher genuinely.
Now getting a job in Canada in itself is hard, unless you are a specialist of some sort in which case you wont be asking this question. On top of that an immigration will be added problem.
You may want to acquire some work exp and then apply.