you just proved the point! a Sportster IS a girl's bike...

 

I have ridden a Dyna for the past 13 years and am in the process of purchasing a RK. I would love an Ultra Classic but I do not ride enough or take long distant overnight trips, at least not yet, ultra's are a bit out of my price range, and I love the road king look especially with out the windshield. I wear a full face helmet so the wind does not bother me. I would go the rental route as you stated and base your decusion on your experience.