Planning to Buy a Harley-Davidson

I am planning to buy a Harley-Davidson and have narrowed down my options, based on reviews and personal preference, to two models: the Sportster 48 and the Street Bob. My use of the Harley will be limited to city commutes and occasional leisure rides. I have heard that customers who buy smaller Harleys (Street and Sportster) eventually upgrade to bigger bikes (Dyna and Softail) and I find that confusing. Please advise me.

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