John- welcome - as a fellow age category rider - well a 69 year old and riding for 53 years now you words find lots of resonance here. I have hung onto motorcycles for as long as 48 years - but find that the 800 lb behemoths just are not so much fun any more. Never a Harley fan but an older Suzuki 1400 in the stable which is great for traveling but for running to the corner store give me the Honda 125 every time.
Similarly on the TW - just a terrific all purpose motorcycle with enough jam to run your 15 mile commute within minutes of the time it used to take on the Harley not to say anything about the improvement in gas mileage which your banker loves.
I am a big fan of EBAY for gear - read the ads, decide what you want and then go and find it on ebay.
Glad you have seen the wisdom of slapping on a helmet - there are no locations left n Canada where it is optional - and as I age my reaction time is slowing which translates into - give me all the help I can get.
Enjoyed your posting - keep them coming please.