From Canada to USA - buying used stereo from private sale

Happy New Year everyone! Not sure where to post this! Please move it to the appropriate forum. 

So if I buy anything preowned such as amplifier, DAC, turntable, phonostage, cartridge that are originally made in Europe, what procedure do we (both buyer and seller) follow?  This is obviously for personal use. I (the buyer) am in the US and the potential seller is in Canada. 

1) Let's say the price is less than US $2500 and shipping is less than US $250. How much (if any) customs and other fees do I (buyer) pay? I looked at the Harmonized Tariff Schedule and it went way over my head!!!
2) Is shipping through Canadian mail vs Fedex or UPS makes a big procedural difference?
3) What is the responsibility of the seller and the same of the buyer? 

TIA for inputs!

I sold a DAC to a guy in Canada last week. He paid for shipping to Canada and sent me a PDF with the shipping label. He used these guys,

Now this is into Canada I am not sure about the opposite direction. For Customs he declared a value for the unit I sent him (an interesting number).

His shipment was via UPS.

I am responsible to send him the audio unit in the description I described and showed in photos. I am also responsible for packing the shipping box in the way I described. In my case it was OEM boxes that were doubled boxed.

Might consider stopping by a local UPS & Fedex store and ask what the protocols are; or call their customer service lines to find out. If it was me I'd avoid Canada and US postal services during the pandemic both are having delivery turnaround time problems
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Used does not matter, country of manufacturing sets the tariff (if any). Usually low.  Get close on the tariff code.  You can usually do a basic web search and get something accurate. Taxes will need to be paid going into Canada on sale amount. That is buyers responsibility to pay. You can also have them responsible for duties and taxes. Just a check box on FedEx form. 
As audio2design said, what matters is where the gear was made. Last I dealt with it, gear built in the countries that are partners with the U.S. in the NAFTA free trade agreement, Mexico and Canada, is duty free. So a pair of Paradigm speakers built in Canada should be free of duty. But a pair of ProAc speakers, bought from a seller in Canada but manufactured in England, would incur a duty, determined by the value and the existing trade agreement between the U.S. and England. This is complicated by whether the authority at the port of entry bothers to check and is able to figure out what they’re dealing with. That’s often not the case. So the answer to your questions is, it depends.
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Canada is not trouble.

I’ve literally shipped thousands of items into the USA.

UPS and FED-EX are the ’easier’ to deal with, regarding the paperwork filing and filling and the guarantee of delivery...

Whereas Canada Post to USPS and then delivery to you, is more tricky and fraught with potential hassles and problems, due to learning to navigate the issues and paperwork. But also less likely to get dinged for the duties and taxes. Depends on the given item and whatnot.

Smart money is on UPS and FED-EX as a shipping method.

Especially if one is unfamiliar with the shipping scenarios and their possible good and bad bits. Which your OP flat out states, thus, it’s UPS or FED-EX for you.

I’m fine with any of them or all, as I’ve got the battle scars that taught me how it all works and shifts about.

Correct regarding no charges for used gear. Also correct about country of origin. 
I purchased Audio Note dac from Canada and paid tariff based on UK rates.

Agree to go with UPS or FedEx, but be prepared to pay COD for tariff. If there is a tariff on your item make sure to have cash on hand, credit card was a  PITA.

I have done well from Canada, and, I had a true disaster.

think protection.

CREDIT CARD: use your best most protective credit card for the payment to paypal then to seller. you might need to change your preferred payment options temporarily to your card.

PAYPAL: only gives protection for GOODS, therefore you need an invoice from the seller.

If you simply send money, it is like sending money to friends or family, no coverage.

EBAY: sold PayPal, and if you give eBay your bank's information, then they send money to your bank, skipping PayPal fees

even if seller asks for you to pay his additional fees, I think it is worth it to get protection.

INSURANCE: the seller buys the insurance, and the seller must make any damage claim. The item will need to be returned to seller's freight company for evaluation. Improper packaging might be an issue, so, keep packking materials, pay attention, i.e. take photos as it comes out of the box.

VINTAGE: do not let seller put vintage on the invoice or description, as, after the fact, after selling seller insurance, UPS Canada said: "we don't insure vintage".
I agree, Canada is not trouble, my post about the tariff rules was only to give a simplified explanation of the process. I've bought and sold lots of items without problems to and from Canada through FedEx, UPS and Canada Post as well as driving them back through the border crossings when I lived in Seattle. 
Stuff can happen in any country but in general , Canada is one of the worlds most honest countries .   I/10th US crime rate .

  I am a Physician.  For years our seniors were encouraged to buy their expensive medications through Canada.  Then these scamming rings started in Toronto sending back fake pills for our Grandparents money.  For years the Canadian government did little to nothing to shut them down.
   I grew up in Detroit, and yes back before 9/11 we would cross into Canada for lunch or something for a totally different experience.  But evil lurks everywhere
True Doc , I am a Patient 85 years old. I took car loads of other elders
up to Thunder Bay ON till the borders were closed and never had a problem. I take only aspirin my self .
The most evil thing in the USA is the entire medical system and the
US does nothing about it and from where i sit, never will.
All we should do is adopt the German System , which I used for 20 years.It is not socialist medicine , there were a dozen German plans , you could
pick who you wanted and what you wanted. Almost half the cost of USA with better outcomes .
How is that possible you say, simple . Germany lets NO German med insurer make more than 5 % profit . 5% is good for most corporate bodies and they would like the American 30% but they go along with the
program which is X amount per-capita for what it is.
Average Doc gets what is required per-capita for their office etc and what is thought to be decent living for a Primary Doc in Germany , About 120 thousand Euros . Which were more women that men when I was there.

Of course a German Physician does not go out in the jungle with a HUGE
debt like An American . More like none at all,.3-4 years ago a law was passed( and is enforced ) that no Resident
may work over 10 hours a day, Why?- too many patients were dying .
I know the Hell that is the American system is NOT the fault of the Doctors !I have a very nice young Lady next store than is a UCLA grad and resident . Crying on my shoulder ( virtually)that she has 10 minutes for the patient and 20 for the insurance company . (I already knew that)In Berlin if you need to get into the Siemens tube, you get a note from your primary , cost , 700 Euros .
In Minneapolis it’s around 4 k. . Must be the freight from Berlin where
they are made .

And Canada still has FAR more crime than us.Sometimes it does to take longer to get this or that done in Canadian System but here 40% can’t even get in line here and there you get
no bill at least .And if you come with a stroke or heart failure you do go to the head of the line!

God Bless !

P’S . Please forgive my sloppy writing . I have that middle whatch-amacale that makes you grasp for words you knew in 3rd grade.
Oh , Germany puts the 5 % only on things they consider human rights.
And compared to USA, on such the German people are one .

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Thanks to everyone for sharing either personal experience or other comments! Very much appreciated. I will stop by both Fedex and UPS and ask them. Have a wonderful weekend!
  If you sell something from Canada to someone in the US and accept PayPal you the seller get dinged with the PayPal fee and an additional PayPal fee for the currency exchange from US funds to Canadian funds.
  It's  EMT or I pass on the sale.