Platokidd, we cross border camp pretty much exclusively from March til October. About 90% of our camping is in NY/PA/OH. Crossing the border is a complete non-issue in either direction. We do it about 40 times per year. Then again we have all appropriate paperwork, passports etc.
We've had all sorts of odd questions from time to time, and have had our trailer entered going into the US many times (usually takes about 5 minutes), but no issues.
Luckily we live about 40 minutes from the border and for me I can go over, fill up the truck, jerry can etc and have enough fuel to last me 2 weeks until we return again.
Then there is the cheaper booze (19 bucks for a 24 of beer versus over 30 here in the great white north). etc.
2015 F-350 SRW 6.7 PSD
2014 Crusader 295RST
1 Fantastic DW
1 Amazing DD
1 Beagle that will be missed (RIP Zeus)