Good post, some very strong opinion from 2 point of view.
There are many reasons not to travel somewhere but it all depends on your main reason to go. If you go to get cheap deals and it is not like in the old days, sure you will stop going. If you are in a hurry and drive on bad roads, it will be a hell of a drive. If you drive a rig combination that is 60 foot long on a road made for Volkswagen, well, be prepared to slow down when cornering.
Roads: I have been to Alaska twice, many road portions are very bad, but it was never a factor for not going, I go there for the scenery and wild life and there is plenty. Fuel price is not cheap either, but being able to boondock makes it easier on the wallet.
Fuel price: Welcome to Canada, we beat everybody
You go for nice wheather: It should be OK for many years to come, and Welcome to Canada, we are already sub-freezing, and it will be like that for many months.
Security: I use common sense no matter where I go. There are very dangerous places in North America, just check the news! you will stay home with your guns loaded.
Food: I am sure I will find Wallmart and Costco in Mexico and normally the price are very close to what you in the rest of North America, this is where I will buy the big stuff, the rest will be at the local market. Fish was more expensive in Alaska than the same Wild salmon from AK at Costco in my home town, still I love the fish fresh from the sea at Valdez and did not care to pay more.
Here is a few things that would slow down my decision:
Trash: Well this could be improved, but all the places I went in the Caraibes, Mexico, Belize, Honduras, it is the same.
Bad cops unreliable: This is one big kickoff, who can you trust if you cannot trust the cops.
Border parperwork: Complicated and you never know what an agent will come up with, and this is both ways, going to Mex or coming back to USA!
Military check up: Suspission, You never really know what they are looking for.
Insurance: Expensive if you go for a short period and still, we have insurance already, it is a bit anoying to have to pay over again
Laws: Guilty first, then you have to prove you are not, they could throw you in Jail, scary!
Getting legally robbed from ATM in Cancun: I was charged 58 Can$ to get 40 US$, a 45% charge, the rate from US to Can is about 15% right now, including the credit card charges.