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That looks alright, but is a bit more involved than I'd like at this point. If I did that, I'd want to change to whole front end out for something with thicker tubes like a heritage or something. Then I'd lose the rat/outlaw look my bike has now, which I like.
No way will a 140 fit with the stock fender, especially when you consider you will need a 3 - 3.5" wide wheel. A 120 will fit sometimes if you keep the wheel width down, I'm going to give one a try next year.
Take a look at this thread to get an idea of the real tire sizes and what's involved...
Although not recommended, I've seen 120s on the standard rim but I just run the 90/90 with great results. Wider Wheels are not that expensive on eBay and many come with bearings/spacers already set up.
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