How do I pay?

Nah

Another consideration/situation I ran into regarding UPS shipping Insurance.

I bought JVC TT81 in large Plinth, shipped from Canada. I requested and paid for enough insurance.

It came destroyed, seller had listed 'Vintage', and UPS said, oh, we don't insure Vintage (even though they sold the insurance, denied the claim. Luckily, seller gave full refund (he had packed it in an ols box, not double boxed.

And, because seller bought the insurance (even though I paid him that cost), he had to make the claim, and he coulsd not start that until it got back to Canada, even though UPS USA Damage Claim had inspected it in a regional office here.

New boxes, double box, no description 'vintage'.

The only time I ever paid with a cashier's check was to someone with a lot of feedback, who lives in a city where I have good friend who's be able to track that person down if we need to. And I spoke to him on the phone many times. I wouldn't do it. 

Don't do it.

@elliottbnewcombjr , I am sure it was not easy to go through the whole shipping damage issue.  As you pointed out, the insurance is with the seller/shipper and is like a contract between them and the shipping company.  As a buyer, you really have little protection and are somewhat at the mercy of how the seller handles shipping issues, which goes back to feedback and dealing with honest and reasonable people.  Just another risk of buying used.  IMO, big speakers should be strapped to a pallet.