Elliot, I think your questions are well founded and this is tough subject. I think you as the dealer gets to set the rules. At the very least, the client ought to take care of the equipment and return it in the exact same condition, or pay for repairs.
If the client is very well known and trustworthy, you can skip the deposit and go by the honor system... but, I do know of a very specific case with my local dealer here who was literally duped by someone who befriended him for a long time and then walked away with a full stack of gear on loan; he actually fled the country with it.
On the opposite side, I have had a pair of amps on loan when a family member died overseas and had to fly out on a Sunday night when the store was closed. I would not return for at least 2 weeks. I made every effort to get in touch with the dealer and return it before my flight that same day, and I was successful. It would have looked very bad if I'd just taken off without returning it for two weeks or more, no matter what my relationship with the dealer.
If the client is not well known, it's seems reasonable to take a credit card on file for reference, and even have the client pay for shipping, especially if the equipment is heavy and expensive and cannot be picked up or delivered. But do you bend the rules if he's already bought at least one piece of expensive equipment from you??? Unclear to me. Personally, I tend to pick up most of the loaners myself, except for heavy amps which are delivered to me at no cost, and I just have not bothered to buy new speakers since 2002 or so, so don't know about what would happen in that case. Moreover, in some cases the dealer insists on loaning all other ancillary equipment if necessary, like cables and cords. I have to admit this is VERY nice. From prior discussions on this subject with the dealer, the vast majority of his local clients are trustworthy.
It feels to me that your risk as a dealer is already big enough in letting equipment on loan, and I feel the prospective buyer must carry the burden in some cases. But I can only speak from a consumer's point of view, and I am not a "whale" - I suspect those folks get the white-glove treatment. I do feel there are a lot of trust-based exchanges in this hobby and have witnessed the same. For example, I will pay for the MIT cables I order when I get word they are about to ship and before I take delivery. My last such transaction was this past Thanksgiving and I sent payment on Thanksgiving day. It feels like the honor system works very well with local dealers and at least with the people I interact with - and that's because they are just very good and courteous people. For remote dealers, I've had to pay up front and got a refund very promptly when I returned what I didn't buy.
I have a feeling you have a lot more to say about this, so looking forward to your thoughts and experiences.
