But my question is not focused on the destination more so the process involved.
So for any that have actually done this, what advise would you provide and what would you have done differently?
Before you leave Ontario, make sure you get your full driver's abstract from MTO. The one that shows when you first got your driver's license (when you were 16 or 17 years old). Does not have to be certified.
Most provinces you move to will treat you like a new driver and give you crap insurance rates unless you can prove you've held your license for xx years. If you come prepared with your full MTO abstract, you can get your entire Ontario driving history counted for a better insurance rate.
Technically, you will have something like 60-90 days to get your vehicle and driver's license transferred over to the new province's registry, but in reality, there's no enforcement on this. Your Ontario insurance company will probably be on you sooner than the government, as they will not pay out any claims after xx days if you are no longer residing in Ontario but your pink slips says you are. You will most likely need to safety certify your vehicle again to register it in your new home province. Motorcycles may be exempt from this safety cert requirement.
The minute you get your new plates, call MTO and have them take your old ownership information out of their system. This will ensure you don't get erroneously billed for any parking or toll charges, because those will be a bear to dispute if you're living in another province.
Depending on the province, health benefits only kick in about 90-180 days after you've moved. But OHIP will still cover you in the meantime. As soon as you're eligible, get your new health card. Make sure you can prove residency by having a rental agreement, or utilities bill dated to the earliest date you can, to prove eligibility.
As for cell service, most people these days just end up keeping their old number. I have a Squamish number from when we first moved to BC, even though I'm in the interior now. All my neighbours still have their old 416, 905 and 403 numbers. Free Canada-wide calling makes the exchange a moot point these days. The only reason why you'd switch to another provider is if they don't have adequate coverage where you live or work.
For snail mail, contact Canada Post and have them forward all your old mail to your new address. They will do this across provinces for either 4 or 12 months. More cost-effective to do it for a year, and then whatever mail comes in that you've forgotten to update, you have a full annual billing cycle to fix that.
If you don't already have housing lined up and don't know which neighbourhood to settle in, use AirBnb and get a 1-2 week rental to try out different neighbourhoods around the city you want to move to. It's very difficult getting an idea of what a neighbourhood will be like just by flying in and visiting for a couple of days: things like traffic patterns/congestion during different times of day and week, noise, proximity/quality of services, demographic of the people who live in the area. While you are trying different places out, you can keep most of your belongings in storage until you settle on a permanent place to move to.