Hi Jordan,
I am so glad you are moving to Winnipeg! It will be great to live in the same city again.
You asked me which area is good for living. I think Osborne Village is best for you. It is close to downtown and there are many cafes and shops. Also there is a park near there, so it is good for your dog. The rent there is not too cheap but it is okay. I think you will like it.
About renting, you should start to look early because good apartments go very fast. Be careful, some ads are fake, so don't send money before you see the place. Also the winter is very cold here, so ask about the heat.
When you arrive I can help you to move your things. I am free in weekends. You can also stay in my place for few days if you need.
See you soon! Mei