I think your note on tolerance levels is right on the mark! I grew up in MI, yea, it gets cold there, but I enjoyed it (at the time.)
Lived 18 years in FL and the last 3 in AL. I think my cold tolerance is shot! I recall my first few years in FL... we made it a point to go to the beach for Christmas, and we swam! About year 5, all that changed! I do think alot of it has to do with how the humidity in the south makes the temps feel much colder than they actually are.
OK... now.... what do I need to be doing to protect myself from the wind? Again, I have the HH Desert Rat, with the oversized fly (not the standard), a RidgeRest pad, older model KAQ, and a MontBell 15* stretch bag. As a side note... I need to be warm to sleep!
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