I have sold things and done pickup in my garage, I have sold things and done pickup at my office building in the parking lot (there are probably as many cameras there as in most parking lots nowadays), I have sold items and done pickup at my house with delivery of the remaining items to the buyer's location. I've accidentally sent people to really sketchy neighborhoods by mixing up "Street" and "Avenue" [eek]
My purchases have been the same way, with most picked up from the buyer's house, usually for transport reasons. Literally all of my in-person used Festool purchases have been direct from the seller's workshop (OF 1400, looked at but passed on a Connector set, MFTs, SYS-Roll...).
For the most part, if I'm selling something for more than $100 and it's difficult to transport, I'll vet the buyer as much as possible and then provide my home address 1-2 hours before the arranged pickup time. If it's something small and easy to transport and not worth much, I'll arrange handoff at my office in the parking lot. If it's really not worth much, I will either only ship it or I'll just donate it and not bother with the hassle.
When I sold my motorcycle, the buyer came to my house 2 or 3 times. I've sold two junker cars for parts as well: one I met the buyer at a gas station and got a ride home from my insurance agent, the other was to someone I knew from an enthusiast mailserv/forum, and he came to my house to trailer it away (he actually had been waiting for me to sell it).
Used electronics seem to attract all sorts of people. Used junk cars attract more attention than it's almost worth attracting. Used Mid-century furniture attracts a very certain kind of person and those sales almost always seemed to go the smoothest. Used Festool likely attracts a certain kind of buyer as well, and likely not as varied as used buyers of big box brands.
