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You didn't mention a budget so my recommendation would be to buy a new Indian. For what you described as your riding routine, it would be perfect and it will be a valuable piece to hand down to your grandson. Now if you DO have a budget, then I would agree with the poster that suggested a Honda. Boxers don't like 100 mile rides in traffic!
You can?????????
I REALLY must be doing this retirement thing wrong!
It depends on how you set your priorities.
I'd really recommend against buying a new BMW. There are way too many late model w/low miles examples on Cycletrader.com, Craigslist, eBay, etc., where you won't take the new bike hit that you do when buying from a dealer. You could end up buying the bike of your dreams for about 60 to 70% of the cost of a new bike.
Good luck with your decision.
Why an Airhead? Because if you really, really plan to take just short trips, not really rack up the miles and then hand it over to the grandson, it will be just fine. The cost for a well maintained R100 or R80 will max out at six grand unless you absolutely have to have a pristine R90S. It will be re-buildable forever. You can tinker with it and your grandson can watch and learn. It will be worth more (in $$ than when you bought it)and meaning when you hand over the keys. On the down side, you will not have ABS, the most modern suspension system, tripmeter, or pretensions that you can take off and go around the world on it ((except that a lot of people did ).
YMMV
Mac
F800 something - ST, GT whatever it is called this year.