Issues off the top of my head aren't strictly winter issues, but winter makes them more challenging:
Where will you store the trailer once you take it off the lot?
When can you schedule a thorough (warm & dry) PDI at the dealer?
Does your dealer charge/have issues with your trailer staying on his lot?
Sherm & Terry w/rescue Eydie (min Schnauzer) & Charley (std Poodle)
2015 Jay Flight 27RLS, GY Endurance (E), Days: 102 '15, 90 '16, 80 '17, 161 '18
2006 Ford F350 PSD, 4WD, CC, LB, SRW, Cmpr. pkg, Equal-i-zer 4-p, Continental ContiTrac TR