I love it when a deal comes together locally. Buying remotely is a little risky because you can't inspect the board first, and there's always shipping concerns. Tons of pictures help, but there's always the fear of getting burned. The last board I sold through the forum ended up being a local sale. That was a nice surprise. The last board I bought from a private seller was from a forum member I trusted. That transaction was excellent.

 

I have sold a SHIT TON of used gear online. The last few years I've ONLY accepted Venmo for payment transactions. Since I take really good care of my gear, I've never had a buyer complain about quality or shipping damage. If you have concerns about the trustworthiness of a buyer, get as much info as you can up front -- cell phone number, mailing address, etc. Request photos of the packed and addressed (to you) item, and of the shipping receipt with tracking info.

That being said, I rarely buy used gear online. And I would NEVER buy a used snowboard sight unseen. There's just too many good deals out there on brand new last year's models if you're willing to dig a little, especially with 21/22 models about to drop. Some of my local shops are currently selling last years left over boards at 40% off.

 

I guess you have to weigh out if saving money on a board is worth the risk. If you can afford to lose $300 and can still snowboard, it might be worth it. If it's your first board and all the money you have in the world and won't be able to ride this winter, then maybe find one locally.
I've only bought boards new or local, but I have shipped some to strangers just like you. One of them turned out to be a guy on this forum which was a cool little surprise.

 

I've sold or bought snowboard gear on unregulated online marketplaces a couple dozen times over the past 15 years. Various forums, subreddits, and Facebook groups. Only once had a minor problem, a busted seam on a set of $30 gloves. Wasn't a big deal.

Just do basic due diligence, look into the person's post history. If they're brand new, be on guard. If you sense any sketchiness, insist on and pay the extra 3% on Paypal for buyer protection. FWIW I almost always just do Friends and Family to save the fee. Paid it once or twice and never ran into problems.