What do you mean by hassle? The processing time is roughly the same no matter where you land. Of course if you land at a big airport like Pearson you may wait a while longer as there may be many people in line ahead of you. Toronto and Vancouver should be equally busy (roughly speaking), Calgary is likely to be less busy.
If you're flying to Winnipeg from Manila, it doesn't make much sense to fly to Toronto and then fly back (unless you get a really great deal). Calgary might be best, or Vancouver.
You can pick any port of entry, decide based on what kinds of flight you get.