We have an 11 Lexus convertible that was my daily commuter (1 mile, HA! HA!) My fun truck was a 04 Ford F150 that I loved, but DS needed a vehicle. We have an 08 Ram diesel to haul the travel trailer and other stuff, including dump runs, but it is not comfortable for traveling. We bought an 18 Highlander new (I loathe repairs) that I love and will keep for 100k+ miles. Our 2 motorcycles bought before retirement and 2 boats were bought after retirement, all used.
DH retired 2014.
Sold my business in '16 and retired 5-17!