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How difficult is it to mount a rear tubeless tire? 180/55B18. I do not have tire mounting machine. Is it worth the hassle? Do I need to get it balanced? If yes, do dina beads work?

Stealer wants $296 for tire plus $80 mount and balance. Seems high to me.
 

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Boy, you got that right(stealer), a lot of smaller shops are around $25 - $30 bucks to install new tire. You pull it off the bike. maybe thier price is pulling your wheel off . Then it's not a bad price.
 

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I have mounted my own tires for the last couple of years. I will be honest, the 180/55-18 is probably the hardest tire out of any in the HD line-up.

The sidewall profile is low and the tire is stiff. I finally broke down and bought a cyclehill tire changer and that made the job unbelievably easy (at least compared to the old tire iron method).

You should be able to do the job, but for your first attempt you will have a challenge on your hands.
 
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