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At 38 you barely even come in above the median age on this forum so forget being "too old".
Don't rule out the sentimental attachment to the cruiser. Getting rid of it could haunt you later. Of course it is possible that you could form as strong an attachment to a Twin.
Resale in 5 years is anybody's guess. But the bottom could drop out on the cruiser's value as well so either way is a gamble. I would not worry about resale either way.
There are several guys here that haul trailers with their Twin. A hitch and light trailer is a viable option. Just don't expect to pull bigger loads.
Some snow tires coupled with basic driving skills and these things are a beast in the winter (Canada).
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Racecar spelled backwards is Racecar, because Racecar.
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