ironore,
Whether you're going to be using a phone you got from Speakout, or another phone, you will still have to buy a Speakout SIM card – either from someone who is selling one, or from Speakout which you will have to buy together with the phone.
I'd suggest going to a 7-11 store, and looking at the display in case they have a plastic 'dummy' phone which you can pick up, etc etc. If you like one of the available phones (there are only 3 to choose from – Nokia 1208, 2760, or 5200), then you can either buy the SIM and phone together at 7-11, or see if someone is selling one on this forum for a bit less.
If you don't like any of the 3 phones that Speakout sells, then you'll have to do 2 things:
1. Buy a SIM card from someone on this forum or buy a SIM card and phone from 7-11 and just use the SIM card
2. Buy a GSM phone that will work with a Speakout SIM. (either an unlocked GSM phone or one that is locked to Rogers). Then place the SIM card into that phone.
If price is a concern, then I suggest buying a Speakout phone and SIM together, either from 7-11 or this forum.
Plus every so often Speakout has this offer "Buy $100 of airtime, get $75 off a phone". Since their cheapest phone/SIM combo is $75, the total cost will be $100+tax. Most likely this promo will return in December, but that hasn't been confirmed yet. If you can wait a month or so, I'd suggest waiting, and buy both of your phones that way.
Either way, I would suggest going to a 7-11 or at least the 7-11 website and choose which phone is best for you. The Nokia 1208 is the least expensive, but the screen and keypad are a little small. When I was buying a phone for my dad, I got him the Nokia 2760 flip phone – part of the reason was because the screen and keypad were bigger. I paid about $25-$35 more, but it's easier for him to use in my opinion.