When I buy or sell something (used), it's cash only, either way except for something over $20k or so. I bought 3 used vehicles last year, two were under $20k, handed the seller cash in an envelope and told them to count it while I watched. The third was a significant amount, the seller was good with a certified check from my credit union.
I sold two vehicles last year, both less than $10k and I told the buyers upfront that they needed to bring cash. There was not a problem.
I understand woodworking tools are a little less rampant than cars, but like you said, these are old school folks. You need to learn how to read people, learn how to figure out if they are shady or not and whether you want to do business with them. I bought a vehicle last Saturday, sight unseen but in talking to him on the phone, text messages and talking with the shop he said he had it serviced at, I was put at ease fairly early on. I brought cash and had no problem with it. We met at a new car dealer where he was buying a new $65k vehicle... The auto shop where he had the vehicle serviced told me "these are good people. I'd buy a car from him before anyone in my family."
Anyway, most people won't even speak to each other on the street, it's a shame. Learn how to deal with people. I'm not buying anything from anyone I don't like or think is shady. If they can't carry on a reasonable, intelligent conversation about something they want to sell to me, I don't want it.... it speaks volumes about how they cared for it while they had it.