I commute to Portland from Sunriver 2x per month. I struggle with whether to buy an airplane. Drive is 3+15. S21 to UAO would be about an hour +/- depending on the bird. But by the time I drive to the hanger, preflight, get the plane out and ready, get the car at the other end, yada, yada, yada... I might save an hour on the trip door-to-door. The route crosses the Cascades so it wouldn't be a reliable all-weather flight - or even a night flight necessarily - unless I was in a FIKI twin. Hard to justify that expense for the hour saved. But then I remember I'd be flying and it becomes more justifiable.
Honestly I'd be happy with a little Super Cub (or equiv). But Mrs. Overlander is highly into family activities, and rightly so. I have three kids 10, 8, and 6. So we're talking Bonanza, Cherokee Six, C210/206. Or Seneca, Barron, 310. Things get expensive quick when you need six seats and want to cross mountains at night in the winter...
The sexiest thing Mrs. Overlander ever said to me was when her out-of-state mother was ill: 'you know, I really wish we had an airplane'... I should have struck that iron when it was hot.