I live in Canada and want to buy an older Harley Davidson from the USA?

Some minor market equipment restrictions, main thing is the 17% VAT that becomes import tariff for some used vehicles- Canadian tax people have market price based on top condition retail price, not Kelly blue book wholesale for Rat bikes. Inspection requirements is another minor hassle- especially with the Harleys even older models- emissions laws and check for stolen parts, numbers. It can be done fairly easily if you go through dealer/broker and have the money. Private party transfer sale is more time and hassle, save some money for brokers- but will still have tarrif and inspection fees.

No one here could possibly tell how much that would be "Worth it" to you. It is a personal subjective judgement call that only you can know the answer to.