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Definitely recommend go South first, then West. Be aware of the weather every day for your planned route. There is always a big ice storm in the KS/OK/MO area in late Jan/ early Feb. Almost set your clock by it.
I can't imagine trying to tow more than 300, maybe 350 miles/day, max, for an extended period of several days. Maybe 400 the first day to get South, but take it easier thereafter.
I ran a short "Streets and Trips" map program for the route and it shows, if you go south at first, I-81 from Syracuse all the way to Knoxville, TN, then I-40 all the way to Santa Rosa, NM, just short of Albuquerque. Then US 54 from Santa Rosa, NM to Alamogordo. It shows 39 hours DRIVING TIME at the somewhat reduced speeds you will want/need to tow at. 6 and 1/2 travel days....... Don't push it!! WATCH THE WEATHER FORECASTS !!!
Mornings in Alamogordo can be very cool, and usually warm up nicely during the day...layers are the clothing requirements. Wind can be a problem at times out there. The AF Base just south of Alamogordo, Holloman, is small but quite modern and nice.
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