You will need to:

1. Go through passport control
2. Wait for your bags
3. Go through customs
4. Get yourself to T2 either using the shuttle bus that leaves outside arrivals or the SkyTrain which has a station near T1B East security.
5. Check-in
6. Go through passport control
7. Go through security at your departure gate

5 hours should be enough time.

The main risks are a very late/cancelled inbound and/or delays at passport control/bag delivery.