Here's my situation right now. I've just heard about Speak Out and it sounds like a good fit – I just want to make sure it'll work out smoothly.

Right now I'm with bell (no sim card), if I activate a SpeakOut phone can I keep my old phone number for free?

Also if I buy/activate this phone in Vancouver and in a year's time move to Ottawa, will I be able to make this transition easily? Would I have to change my number or pay any extra fees?

Thanks very much!

if I activate a SpeakOut phone can I keep my old phone number for free?

As stated, yes. Note that you have to initiate the port through SO CS, not Bell. Also, makes sure you are off contract with Bell, otherwise they will rape you with an ETF.

Also if I buy/activate this phone in Vancouver and in a year's time move to Ottawa, will I be able to make this transition easily? Would I have to change my number or pay any extra fees?

You can continue using the phone in Ottawa using your Vancouver number but, of course, you'll pay LD charges. Instead you should call SO CS, tell them you've moved and ask them for a new Ottawa number. There is no charge for this and you won't lose any airtime credits.

The funds will transfer over as long as your on the same sim

Woah, hold on – I think you need to specify that you have a balance to carry over when you call Speakout (as mentioned on this forum in the past). Once you do a number transfer, a new dialout gives you the same "you now have $5 for activating" kinda message. If they make a note of your account balance ahead of time, they can apparently transfer it for you.

Save yourself the potential worry and don't apply the $100 yet – do the number transfer first.