I'll preface my post with saying that compared to our neighbours south of the border, Canadian services are somewhat ridiculously priced for what little you get. Be prepared to pay a lot more than what you did for probably less than what you had.

To my knowledge, no cross-border family-type plan exists. You can get add-ons that will drop your long distance costs a bit (either unlimited calling or usually around $0.05/minute) but families calling you will still have to pay their long distance charges and, depending on the provider, you will also be billed long distance charges for an incoming long distance call. Check with your provider and ask exactly how they handle long distance calls and calling outside/within your calling area.

That said, I'm with Koodo Mobile (a subsidiary of Telus). You pay month to month and aren't locked into a contract, plus you can add/change your plans whenever you want. The only downside is that you have to either pay for the phones up front or be locked into their pseudo-contract, otherwise known as their "tab." Since Koodo uses Telus' network, you're pretty much guaranteed coverage throughout all of Canada and even some parts of the US.

A more recent prepaid service is Wind. I haven't heard much about them but they're coverage is limited to a handful of Canadian cities. From what I can see, their offerings are pretty reasonably priced.

The big three in Canada are Bell, Rogers (who also owns Fido) and Telus. They'll probably offer a lot more but their prepaid plans are terrible. If you don't want a contract, you can opt to buy the phone up front and pay on a monthy basis. You can get phones for cheap but you will have to be locked into a one to three-year contract.