Question - How do you flightplan extended spousal cross-country flights?

[n86121]

Software suggests my RSTOL T337D
could get us DCA to DEN in ~7-10 hours, depending on winds.

It is about 7 hours door-to-door commercial.

Stressful, but "You leave the driving to them."

My wife's eyes start rolling at ~4 hours in the 337.

My main unknown is, "How many back-to-back legs would she tolerate, before destroying 30+ years of marriage?"

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OPTION #1 - GRIND X COUNTRY ALL IN ONE DAY?

In spring / summer we could leave early and get to DEN before nightfall.
Refreshed or exhausted?

OPTION #2 - BREAK INTO TWO DAYS?

Maybe plan two 3-4 hour legs the first day.
No specific destinations in mind, just go until tired,
Let Amex Platinum solve the logistics.

A fancy dinner and a good night's sleep in a swanky hotel,
then finish the next morning?

OPTION #3 - TRY IT SOLO FIRST?

Buy her an airline ticket and see who gets there less stressed?
If I get tired, or decide to turn around, less egg on face.

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QUESTION - How do you flightplan extended spousal flights?