I went through the same thing trying to figure out how to get CL sellers to feel comfortable shipping and item. I lost out on several deals because I didn't have everything lined up when I first started attempting to do the shipping thing through CL.
I've had CL items shipped from Denver, Boston and a couple of other places.
I had the seller send more pics so I knew they had the item. I talked to the seller quite a bit and got the feeling they were on the level and to let them know that I was on the level. I faxed my driver's license one time and got theirs in return.
I then got the size and weight of the item. I also got the seller to agree to:
1) allow UPS to pack and ship the item,
2) take Paypal after the UPS tracking # was issued(UPS has a computer that can be used to check your Paypal account)
3) and also to ship the item based on the following:
a) I got the seller's street name and found the nearest UPS store. Or maybe the seller knows the location.
b) I called the store and spoke to the manager. I let him/her know that I would be paying for shipping by credit card for an item that someone would be bringing in.
c) I got the manager to agree that I could speak with whomever was clerking at the time of shipment so I could have them describe the item to me. Note: With the ease of sending cell phone pictures, maybe someone at UPS could send you pictures of the item to be shipped)
d) I also told the manager I would have the seller call me when he arrived at the store.
e) I called the UPS store clerk and had them describe the item to me and if it was the item, I had them pack it.
f) Note: Packing should have NO peanuts-only about 6 inches thick of large bubble wrap around the entire item including the corners. For an amp, I also had small bubble wrap placed in and around the inside of the amp(especially for tubes). They can get a box to fit by adding more bubble wrap if necessary
g) I then paid for the packing/shipping.
h) I contacted the seller after the UPS tracking # was issued ( I had the clerk give me the #), I then dropped a payment into the seller's paypal account which he could check online at the time.
i) After everything was cleared by the buyer/UPS, the transaction was complete.
Be sure and have the seller include a signed receipt with the item (including all the details). I didn't for a couple of items and had to request a receipt after the fact.
Note: for the item I had shipped from Boston, I used a freight consolidator and the speaker cab was freighted out to Los Angeles. There were additional charges to get the freight from the distribution center to my house and to have the pallet moved from the truck to my garage.
IME, there are no refunds/returns on CL items shipped unless the seller agrees. Even if he/she agrees there's really no practical way to make pursue someone who won't give you your money back.
BTW, I've had worse luck with some ebay sellers.
YMMV.