Unfortunately you come from a country that has a high level of visa fraud (i.e. people overstaying their visas). As a result, it will be more difficult for you to be approved than someone from, let's say, Europe.
You will not be able to cover all of your living and tuition expenses by studying while working. You will be lucky if you can cover your living expenses alone. CIC does not expect you to be able to earn enough money while studying to cover all of your tuition and expenses. CIC expects you to either already have sufficient funds or have a source of income (e.g. business back home) that will provide you with these funds.
As for how many years before you can bring your family over (if you leave them back home while you study) - it will be a fair amount. Let's say you take a two year course, then work a year full time to qualify to apply for PR through CEC. Then you must wait another year or more for the PR application to be processed. So I would say you're looking at four years minimum.
If you do not want to be separated from your family then the best approach is to apply for the study visa and include them. There may be a good chance you'll be refused - but there's always a chance that you will be approved.
