no visa business visits usa

Hey all

Looking for insight / thoughts on crossing border via airport multiple times for business. Recently I crossed the land border in NF july 27th and said I was going down for market insight and the agent was nice but gave me a bit of a hard time and said I needed a visa (i explained why I was told i didn’t) and he let me through. I came back september 14th (drove back with my dogs) and was home for 7 days and flew back (sept 21). I used the MPC line and just got a couple extra questions regarding my last visit and why i need to go back again - returned via flight dec 20th, no issues on re entry.

The guy i travel with didn’t have it as good as he was pulled into secondary (which can be multiple things so who knows) and he put his foot down and doesn’t want to travel anymore. This kind of spooked me cause I don’t want to lose access to the US as my wife and I frequent travel there.

My company (canadian company who I’m paid by) said I can come up with my own schedule for visiting and coming home, so now I’m wondering what the best option is to not look “sketchy”. In terms of documentation I read bringing a paystub can be handy? Ive only ever brought a letter from my HR which the agents always laugh at and tell me to tell my HR thats a joke lol.

I have 2 dogs and a wife whos a teacher (pension ticket lol) i’m not fleeing to the states lol! Any help is appreciated. Much love.