This is how I'm doing it too.
With anyone of color light blue and above - I wouldn't think twice about giving them to hold my wallet. I guess there are some exceptions now and then( I think Sartre was light blue? ) but I think it's incredibly rare.
This week alone I got scammed for like $350 from BHW and that's on me because I like to trust people and honestly, I will still keep doing that because those times when the trust given comes back is way more valuable than money spent to feed the scammer.
If I would need to spend $1k, then some due diligence is a must for sure, to check reviews, business history, overall public communication style. Because $1k isn't much in how valuable a well-built BHW profile can be.
for 5k worth of product? I would be careful and probably ask to go 50/50 or pay by milestones if that's my first time dealing with the seller.