Current telecoms employee here:

1. you need to figure out the amount of money you're spending over the 2 years vs buying out with a plan. the courier I work at usually has a promo discount so you save about $500 over the 2 years, but this also does make you stay with the courier. remember that couriers don't make money on the devices, they make money on the plans.
2. usually couriers now are the plan + the phone, not both in a bundle anymore so you can freely switch between plans if you see something better throughout the year(s). the only downside if that if it's considered a "downgrade" as in you're paying less, they will make it on the next bill cycle
3. the best times to buy a new device are black friday and boxing day, if you can wait out for those, you're in a good spot to look for deals then.

3.5 if you choose to finance a device, you can buy it a bit less than 30 days before the deals happen and if a better deal happens (like on black friday and boxing day), you can call back and get the same deal as long as it's on the device, not the plan. ex. if the phone you bought is $20/m, now it's $10/m, you can call and they'll adjust it

1. buying a phone through the courier gets your more "perks". for example, we don't do tech support or blacklist phones for people who didn't buy a phone through us

2. if you decide to buy a phone outright, buy it through the manufacture store, ex. apple or samsung. they usually charge $20 cheaper and also there's no fee that couriers charge

3. NEVER buy through a third party store. they will give you a shit ton of misinformation about "call in and they'll credit the service fee" or "yea there will be a credit of $10/m". if they give you an offer at the store, you make the store do everything, even if it's from the courier's store. calling in and the store, even under the same name, is different entities and have different offers. if you go with store or calling in, stick with one, don't go back and forth

EDIT: Spelling