Welcome to the wandering ways.
1. In my experience Canadians are generally well received in the lower 48. So no issues there. A month at each destination is a pretty good plan, it means you are willing to make reservations in advance and you will spend enough time at each destination to get to know it well. Because of the time you are willing to spend at each destination you don't have to be exactly in the most desired locations. We have found that in the last 3 years the number of RV'ers has increased and desired locations tend to book up months in advance, shutting out folks that are willing to spend a bit more time there. But, it also means that RV parks an hours drive away remain open and are quite happy to have your business.
Which states/parks to visit? Holly molly, there is so much it is impossible to list. Mostly it depends on where your personal interests lay. All of the states have something of interest to explore. History, culture, nature, adventure... you can't go anywhere without running into something interesting.
2. First TV. Most medium size cities and larger have broadcast TV that you can pick up with the stock TV system that came with your RV. It's free, just do a channel search and stuff will pop up. IMHO it's mostly junk you would never want to watch, but to each there own. We all have our own interests. Next step up is satellite TV, Dish ... ok senior moment... I can't remember the other one. Basically a satellite dish that you set up behind your rig to reach the satellite dishes that offer a few hundred channels of TV. You pay a monthly fee for this. It's limitation is line of sight to the southern horizon. Works pretty good in most locations, but sometimes trees, ridges, buildings, etc block the signal. I think most that watch a lot of TV have workarounds for this. I don't watch much TV, mostly I think todays programming is pure garbage, just my own soapbox on that subject. I'd rather read a book.
3. Cellphones/internet. There is lots and lots of stuff out there on this subject, probably lots smarter folks than me. So I will tell you what we do and why. As far as I know canadian citizens can walk into a local cell phone store and purchase a plan, I don't think residence plays much of a part in it, although I don't know that for a fact. Hopefully some Canadian snow birds can help. Anyway, I spend about $230 US for cellphone and internet. We have two phones, my wifes is on ATT, mine on Verizon. Of the two Verizon works better as we travel about. There are other plans that are cheaper, but they rely on you staying in one place. On my Verizon plan I get 70gb of data on my cell phone without incurring other charges, however, I am restricted to 30 gb of sharing my data via hotspot to my computer, xbox, tv, etc. I also have a "myfi" device, essentially a broadband receiver, that has a limit of 15gb per month download. These devices are advertised as "unlimited data", not true, after the limit is hit the rate of transfer is throttled to a degree that makes them almost unusable. One of my pet peeve's. My wifes ATT plan is similar, 70 gb on her phone, 30 gb shared data. From what I can tell it takes about 2 gb per hour to "stream" a movie or TV show. There will be lots of argument on what I have just said, this is my experience. Others have done better, but I would tend to argue specifics with them. Again, just my personal experience.
4. Several memberships out there, most are pretty good. Let's see; Good Sam, yup, we give them a bunch of money each year. Basic membership will give you a 10% savings on most rack rates. It's so common that most don't check that you are actually members. We have been for many years. I also buy the Platinum Raodside Assistance and the Travel Assist. The former has paid for our RV to be towed 3 times in 10 years and the latter I keep in case I meet an early demise, it will get the RV anyplace my wife needs it to be because I won't be around to make it happen.
We have purchased a lifetime membership with Passport America. The program is a little past it's prime, they offer 50% off rates for a couple of nights stays with lots of conditions, you just have to read the fine print. Many participating RV parks are pretty much substandard, no more than a gravel lot with hookups. But that is ok with us, we use it primarlly while moving from place to place and just need a site with hookups for a night or two.
TT aka Thousand Trails. They offer a multitude of plans. We have purchased the most basic plan when we have identified a specific place we wish to be for an extended period of time. Cheapest plan is around $500 for the year. You are restricted to spending 2 weeks at a location, then you have to leave for 4 days before you can return for another 2 weeks. But you can do that for a whole year for less than what it would cost to spend a month. The key that we found; was to make them guarantee a reservation at you most desired location before you purchase. It either works well or it's a waste of money, just depends on how hard you want to work it.
Escapees, good outfit. I Joined the first few years, but later dropped my membership. It just wasn't for me.
There's a few more out there, you just have to decide if they provide enough service to warrant the expense.
5. Sketchy area. Ok, that's a good subject for whole thread by itself. How do you define that. A couple of good stories. 10 years, 1 theft. We went to lunch at Panera Bread in a busy mall area. Someone popped the lock on the truck and made off with about $3000 worth of stuff, in a busy mall parking lot with security. We have boondocked away from any civilization without incident. Stayed at crowded inner city RV parks without incident. Left the RV at a rest area to get parts for a repair, no problem. Stayed at RV parks where 90% of the occupants where hourly workers barely surviving and living in old RV's because that's all they can afford, no problem. Stayed in an RV park full of transient oil workers, no problem. State and National Parks are well patrolled.
The problems are pretty isolated. Yes, event's occur, it's just not the norm. The RV park we are in tonight had a statement in there welcome sheet that said please ensure you bicycle is under lock and key. There have been reports of bicycle theft in the area. A friend of mine had his motorcycle stolen while we stayed a popular casino resort in Las Vegas. They had a security patrol. He spent a day talking with police etc. to file a report about his stolen motorcycle. Events occur, so he was ready to move on. Next morning the junkies that stole his motorcycle where pushing it past his rig while he was drinking his morning coffee. A quick call to police and they apprehended the junkies, he got his motorcycle back. You can't make that up.
There is the occasional petty theft at RV parks. Most of what I have read about is folks that stay in one place. We move almost constantly. It would be difficult for a petty thief to scout us out for theft, we just aren't there long enough for them to make a plan. Then, when we do stop for an extended period, weeks, months. It's in locations where petty theft is unlikely. Just too far away from desperate people.
1/2023 is a ways off. I am sure things will be a bit different by then. But we spent 5 years working on our retirement dream, now we have been at it for 10 years. A lot has changed in the last 15 years.
Good luck, safe travels!