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I've never been into the cruisers but I can tell you that in general you are usually better off buying a bike that comes stock with the horsepower level you want than you are modifying the engine for more horsepower.* You'll have something that is more reliable, more driveable, and you'll probably spend less money too.
These days my modification money tends to be spent on premium tires and suspension, as they'll actually be of some use.* Blowing cash on making a 140mph bike go 150mph (or in your case with the Harley, a maybe 100 mph bike go 110) doesn't make much sense for street use.
As to the retaining value issue, it sure seems that the big cruiser/custom market has got to have the bottom drop out one of these days.* There are sooooo many of the things around and there is sure a lot of "fad" feel to the things. I suspect that one with 5000 miles on it is considered "high mileage" as a lot of them seem to be used more for posing than riding.
Buy the one you like because you want to ride it, not because it seems like a good investment.* Motorcycling can easily have lots in common with boating in the fashion of "hole in the water surrounded by wood that you throw money into".
cheers,
Michael
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