Well, I cut out the sim according to specs from a template. It inserted perfectly into my Lumia, I had speakout transfer my current number to this card, but I'm getting a "No sim card inserted" message. Any ideas at all what to do next?

I had that happened too because the metal tabs are not contacting the right pins inside the phone. Try cutting the SIM a bit smaller so you can position the SIM in a way that would make contact when you insert it to the phone.

Is there a correct way to cut a speakout sim for a Lumia 900? I'd like to get this right the first time if possible.

Also, do I need to unlock this Roger's lumia for speakout>

You don't need to unlocked your Rogers phone

To cut SO sim to micro sim just look on kijiji someone has ad there to cut normal sim to micro sim for $5 or less

Another way to do it you need to google micro sim template and print it out and tape it on your SO sim and cut it out

Also, do I need to unlock this Roger's lumia for speakout>