Living in Canada, prices are very high. If you are new to smoking, you are going to go to b&m to start and it's hard pressed to find any cuban cigars under 20 dollars. Sure you'll start with a monte 5 or HU majestic for 15 dollars, but you'll soon want to try a Cohiba or partagas. Those are going to run you 20+ all day long, and that's the cheap ones. Then you are going to want to try something special.... And pay 50 dollars. You'll do this until you realize that the ones you really want to smoke all the time are 20, 30, 40 dollars and you'll have to find cheaper ways to smoke those. Forums, etc help you find your way and soon you are buying boxes of sir Winston's for 15.08 a stick.
You see the point is , I have spend 53 dollars for a cigar, was it worth it? I don't know, I loved it? and ended up buying a box of them online at 26 dollars each, and love them... If spend 53 or 26 for the same one , I loved it. It's all relative.
When I go to Cuba next year and buy the same cigar to smoke one afternoon and only pay 13 dollars for it, it's not going to be any better or worst... Depending on some non cost factors.
Again, building a collection and averaging 10 dollars, or 15, or buying singles at B&Ms for 20+ .... It's all relative. How much money do you make, your wife make, where are you, what's happened that day, or week, what is the weather like, what are you pairing it with, what friends are you with, etc etc etc......
To ask what cigars are worth it can't really be answered with a yes or no.....