Sounds to me like you're indulging in a series of missteps, for unknown reasons.
To start with, it's not a requirement to get "scammed $50-100 at each border." That's purely optional. It's so easy these days to look up the legitimate fees and procedures for any border crossing in Latin America--most of the time with photos and even videos telling you which window to go to, where to park, who the ripoff artists are, how much you should pay IF you choose to hire a helper....
Nor is it mandatory to spend "$65usd" on hotels in Mexico. I don't think I've ever spent that much, even when so desperate I took whatever I stumbled across without worrying about the price. Of course, I never stayed overnight in Puerto Penasco. Or in Mazatlan. Something's maybe wrong with your approach....? Or are you living more luxuriously than most?
It's true that aside from el espinoza del diablo up the hill from Mazatlan, you chose one of the more boring routes from all those available, but you don't have to keep on doing it that way. On the other hand, if your goal is to stay warm you're looking at generally chilly mountain weather during the chilliest time of year from Durango south. Personally, I prefer the mountains over the coast--better riding, better people and sights, fewer tourists--but there's no denying there's lots of attractive coast between Durango and Guatemala. Just try not to pay tourist prices for tourist lodging.
Sounds like you paid an appropriate price for a full year's worth of insurance. That's good, and it's a one-time expense to be amortized over a full year. You'll get your TIP deposit back when you leave the country, if that's included in your budget. But tires are best purchased before leaving the Land of the Free, not in Mexico or Central America. Same AFAIK with other consumables, much less serious repair items. I've been too impatient to buy tires in Texas on my way south--I'm always impatient to leave Texas--and then paid the price later on, but I figure that's a choice, not a necessity.
The 800 or so miles (sorry: I mean 1300 km) from the border to Mazatlan ought to use about 60 liters of gas, right? At just over a (US) dollar per liter, same as you pay in Canada? 30CAD should buy you 22 liters of fuel; you must be running it dry if you spend that much per fill-up. Do you have a particularly twitchy throttle hand? Or is the VFR so much less economical than my weary old KLRs and DL?
I'm not here to criticize. I'm really just trying to offer food for thought as you contemplate your trip. I'd be alarmed at the amounts of money you're describing, too. But I'd wonder what you were expecting: would a hundred CAD per day satisfy you? That's what you're really spending, insurance aside. Or $75? You could achieve that by backing off on the hotels and fuel consumption. Lower still would require some hard decisions, but it can certainly be done.
Hope that's helpful, and hope it's taken in the constructive spirit in which it's intended. If not, please just ignore.
Mark
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