I have both sold and purchased a saddle through private sales just recently with trials on both. Both went incredibly smooth with no issues whatsoever. The one I sold was clear across the country to someone in California. The one I purchased was just a couple states away in Texas. Both transactions occurred back to back. Did I get lucky? Perhaps, but if you spent any time on social media and talking to strangers, you can kinda get a feel for people. I advertise on FB marketplace where I can check out their profiles. The horse world is kinda small so I even found a mutual friend/trusted trainer between us.
Both myself and the other seller offered a 7 day trial with full payment including shipping up front through PayPal only. The buyer I sold to asked to speak on the phone, and I was totally open for that. She explained the horse she was buying for and I was as honest and upfront as possible. Saddles are expensive and finding a good deal locally on exactly what you need is not the easiest thing. She sent the money plus shipping. I mailed the saddle the next morning and provided tracking info. PayPal holds the money until you enter tracking info and they can confirm that it has been delivered. 24hrs after delivery, they released the funds, but I didn’t touch them till I knew the sale was for sure. She contacted me 5 days into the trial, let me know she was keeping it, and thanked me for an easy transaction. Once she confirmed, I PayPal’d the seller of the saddle I wanted and we did the exact same process. 4 days in, I let her know I was keeping it.
This was my first time doing the trials, but I got the advice from a friend who’d done the same and sold 2 saddles offering trials.