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Southern Route
What a great topic. Still considering equipment, but think I would include a couple small traps and snares for times when I "hole up" to rest-recuperate-wait out weather-etc. in order to feed myself without using ammunition. Several small metal mirrors would be worth the extra weight as trade items - the edge could be honed for natives to use as a scraping tool.
The southern route would be best for me - weather and familiarity. Start in Charleston, SC through Cherokee Nation (we didn't really piss them off too much until after 1700), end up following Red River through part of Texas, cross NM and pick up the headwaters of the Gila River, follow it to the Colorado. The "bad part" would be crossing through what is now Imperial County, CA along I-8 route, but there are a couple of springs - definitely to be done in winter, cooler temps and more rain.
I'd want to end up in San Diego area - probably around La Jolla Cove. I'd probably include some goggles and a folding pole spear - to feed myself at the Cove while awaiting my time machine (as well as fishing in streams along the way). 18 months would do nicely, but I might allow 2 years for the "unforseen". If I get there early, I just hang out in La Jolla. I'd hate to miss my "pickup"! Details to follow
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