I'm from another city and I'm planning on using Wind mobile when I come to Mac as the plan includes canada wide calling. What I'm wondering is whether I should keep my current number or get a Hamilton number? Would it be inconvenient for others to call/text me if I keep the number of my current city? What features do most peoples plans have?

It depends on where your "current city" is, as well as how often you'll go home, make phone calls, etc.
I didn't bother switching mine, even though it was long distance to call home...I just didn't call home that often, or I used google phone. But, other people from the same city as me did choose to switch.

If you are getting Canada wide calling, then don't bother changing your phone number.

But make sure Wind's cellular coverage in Hamilton is decent because I've heard there quality isnt that great.

Please correct me if i'm wrong