View from the town campground:
Leaving the village:
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Allowing $100/day for everything (hotels, camping, food, etc.), based on your schedule, a 60 day trip will cost you $6000.
Do you actually ever spend that much per day on a multi-week or multi-month tour?
The "field notes" carried by the leader described one campground as "combat camping at its finest."
Ha!........I remember that one near Damariscotta. The notes went on to say "This place is a cross between a world's fair and a campground."
Practice. Learn to ride in rain and wind by getting out and doing it. You quickly learn how to cope with the conditions and learn how to decide when it's time to go home or find cover or grind it out. You also quickly discover what kind of clothing or gear works and what was a waste of money. Do all of that experimentation close to home.
Also a good idea to practice setting up camp in wind and wind-driven rain. You quickly learn how not to let your tent get destroyed, how to keep your gear under the fly till the thing's up, what's important to keep dry and what can get soaked.
As for the weight thing, I am carrying 300# on a 5'7" frame, have been overweight my entire adult life.Gastric bypass will still require that you learn to do what it takes to maintain a healthy weight eventually or else you will ultimately wind up putting the weight back on some years down the road.