Pulling the trigger on pricey equipment

I have the opportunity to purchase a somewhat expensive pair of speakers from a private seller on Audiogon. His feedback is around 30 and mine is around 160. I have never purchased anything this expensive online privately. The speakers will have to be palletized and shipped freight insured. My angst is in I'm sending a lot of money upfront with the hope of receiving the speakers. Are there any suggestions regarding payment (maybe 1/2 upfront and 1/2 upon delivery) or best way to safeguard my money and alleviate some of the emotional stress in this transaction. Is Paypal my best option?
If he is 30, that seems fairly solid. You should also be speaking with him by phone to get a better feel. Paypal is probably your best option for payment.
+1 on what Roxy54 said. I always want to talk on the phone with someone from whom I'm buying something expensive. Arranging palletized shipping is not something I'd want to be nonchalant about. Paypal offers the most buyer protection of any payment scheme I'm aware of when purchasing from a private seller.
Yes PayPal is your best option ..anything else would be complete folly. Just make sure you send money to a recognized PayPal name and address.
If you're that concerned, then don't do this sale and wait for the speaker to become available within driving distance so you can make a face to face transaction.
There are 'Escrow' services. The service holds the money and ony pays it when the buyer gets the items.
Usually escrow services charge a fee. and you would have to do due dilligence on picking one both you and the buyer feel safe with.

Any feeling of worry I would hold off and wait for some near enough you can go there.
Paalletizing speakers is a big deal, and the shipping company has to be really great. Any mistakes and you get busted junk.

The most I have spent here is $2,400 and that was delivered by the owner to my home.
I would be pretty worried with a lot more than that floating on a promise cross country.
If you do it, just make sure you are safe.

I paid over $1000 cash for a pair of speakers once. We met in a Barnes and Noble store in a mall, but the speakers were in his car trunk outside. And it was dark. But he was a real gentleman and it worked out.

I paid $8000 cash for a pair of amps once. It was out of my state in his town. We met at his home (so I would know where he lived). The amps were in his car trunk in boxes. He showed me the boxes and we drove to his bank and he deposited the cash. Then we moved the boxes into my car. At least it was broad daylight. Still using those amps now.

Don't know if I'd do this again.
The biggest ticket item I have bought here was 3700.00 for a pair of speakers. The seller had a solid rating and we spoke by phone before concluding the transaction. I paid via PayPal on a Sunday evening and the seller shipped the speakers out the next morning via Fed Ex freight. I received the speakers 4 days later in absolutely perfect condition. I would do it again in a heartbeat.
Do not just look at feedback numbers. Read the comments. Did the seller keep his promises so conscientiously that they merited comment? Did he go out of his way to package securely? Was equipment rated fairly or conservatively? Both equipment ratings would result in the same positive feedback score but might be differentiated in the comments. e.g. "item was as described" "item was better than described".

For example feedback for me frequently mentions the pristine condition of equipment I sell. I have several pairs of white cotton gloves located near my rack. The result is equipment that looks like it just came out of the box. I still tend to underrate due to age. I also ship the same day or one day after receiving payment. I do not get bonus points for that in my rating but it does show up in the comments section.
I agree with Roxy. Speaking on the phone is key, getting a sense of confidence. Reading the comments on feedback too. I've performed transactions over $10k on audiogon before (both selling and buying). The most expensive purchases, however, were from dealers. I think the 50/50 is reasonable, though I've never done it or the escrow (also reasonable, especially if you pay the Escrow fee). For really expensive deals that I've fantasized about, I have though about flying out and overseeing the deal in person. Palletizing is great, and not too difficult with a good shipper (e.g. Pilot Air). I've received 2 pairs of Avalon speakers in crates palletized - very little worry about damage.
Feedback rating and comments go along way. However patience and a tank of gas makes for the best feeling of confidence in a high priced private deal. From a dealer I would not be concerned.
I wired $30k to a guy in Singapore for a high end turntable. He had very good feedback; much more than 30 but still a lot of money to wire to a guy I didn't know and overseas to boot. 4 days later the turntable arrived via DHL as promised. Best part is the shipping was included. Go with your gut after a long conversation, or fly out and watch them be loaded on the truck! Might be cheaper than the escrow service and more fun!
I have never had a problem on Audiogon. Everyone has been courteous and efficient and no deal has gone sour. I really do believe if you are polite and do what you say, when you say, you are more likely to be treated in the same way.

What you have to watch out for, is an A/C being taken over by a fraudster. That happened to me on E-bay about 10 years ago, my password was changed to shut me out and about $1000,000 of kit, including BMW's, Audi's, high end speakers, put on sale with a 3 day auction. Luckily I jumped up and down and waved my arms and eventually E-bay stopped the transactions.
THis is a very interesting and valuable topic!

One takes a huge risk buying expensive used stuff that has to be shipped, whether here or anywhere. I shy away from larger or more expensive items that have to be shipped in general and look more for sellers within driving distance that are open to meet face to face as needed.

I am soaking it in and trying to learn.

What protection exactly does Paypal provide in a case like this?

Using escrow sounds like a smart option, but I have never done this. IS there a specific company /service that is recommended?
I used PayPal to purchase a 780.00 preamp. The seller tried his best to scam me buy not answering my Emails and not answering his phone. I sent cash through the PayPal system to a recognized name and address. I contacted PayPal and they froze his ACCOUNT that day. In 14 days the money was returned back into my account from his. That's the protection PayPal gives if you send payment to a PayPal recognized account.
You should also check into what type of insurance can be obtained on the shipment.

If you are nervous, you could also have the buyer take photos of the equipment with a current newspaper (to show that they actually have the equipment). ETC.
I would not buy anything expensive without viewing it and listening to it.
Problem with PayPal is that silly buyers can use it to freeze the payment for no good reason and trust me when I say no good reason. I had a strange dude do this to me with a lame reason and PayPal just listened to the buyer and immediately froze by PayPal. Use PayPal at your own risk and know as a seller you have no protection from the crazies with any lame reason to cause trouble.
I've been fortunate on both the buy and sell side of many deals. Check my feedback.

For example, I just sold my ARC VS-115 amp for a fair piece of coin to a new member (no feedback) who lives on the west coast. I had a good feeling about the guy, especially after a live conversation or two. I even took his personal check and shipped before it cleared. Thank goodness .. no issues on either side of the deal. Check cleared and amp made it to the west coast in A-1 shape.

I also sold speakers (100 pounds each) that had to be palletized. Again, no problems on either side of the deal. Money cleared and speakers made it without a scratch.

I suppose member reviews are helpful, a live conversation is helpful and a little bit of luck is VERY helpful.
Be patient and wait for the item to be available within driving distance. I drove halfway to Maryland from Jersey for my speakers.
I would agree with Bifwynne - exchange telephone #s & call the seller. Have an extended chat with him. It will give you a feel for the person.
Like Bifwynne, I've been very lucky in my sales & purchases on A'gon but each time I called the person & chatted with them. That always gave me either a good feeling (yes, I want to buy from/sell to this person) or a bad feeling (no, this sale is not happening with this person).
Your angst is very understanding & many of us empathize. All the best....
If I was buying gear which was more than a few hundred dollars, especially if several (or more) thousands, I'd drive/fly to the seller's and meet in person to see/touch/hear the gear first. Less risk once the seller knows you not only know where they live, but are also willing to pay them a personal visit, if necessary.
I think everyone who uses Audiogon shares and empathizes with your concerns. Fortunately, I have had only enjoyable transactions here but it does take a degree of luck and almost a second sense about the party on the other end of the transaction. The most important thing is to try to strike up a conversation with the party you will be transacting with, both through e-mails and on the phone and follow your instincts. I can think of a few occasion's where I was interest in purchasing something and the response just put me off and made me wary. Obviously, in those cases I just drop it. Not worth the risk, and indeed there is a risk factor. On the other hand, it provides you with the opportunity of putting together a system of a caliber you might otherwise not be able to afford to.
What about using Facetime. That way you get the meet the seller... and actually see the equipment you're buying.
I like that Facetime suggestion.

Also, a feedback score of 30 is, what, 8 transactions or something like that. Not so many, but okay. I always look at the timing of the feedback to see if the seller has been active for awhile, or has it appeared all of a sudden?

Contact some of his/her feedback providers and ask them to verify and for more detail. Any names on there you recognize from the forums or your own transactions?

I usually try to check out a seller (buyers too) via LinkedIn and Google. There could still be fraud if someone is pretending to be someone else, but it's comforting to see that the person is an engineer or physician or whatever. If you have a physical address, there's even more you can do online.
Love to pull the trigger on high end stuff!!
"What about using Facetime. That way you get the meet the seller... and actually see the equipment you're buying. "

That's a really good suggestion!

Facetime sound quality: not hifi though.... :^)
The hardest high $$ sale I ever did was with a Vietnamese fellow who was acting as an agent for a richer guy in Vietnam for a CAT JL2 amplifier ($5k). He had no feedback, and he claimed no account because of Agon international issues. I have excellent feedback and lots of it. I told them that the only way I'd do the deal was through wire transfer and even then, after it fully cleared. They didn't like it but ultimately complied. I know that is the opposite situation, but it is an example of where poor communication (he had poor English) didn't support trust at all.