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Besides whether or not you'll make yourselves miserable, there is another very important consideration that you're apparently ignoring - safety. In order to make the 2200+ miles from Milwaukee to San Jose in 3½ days, on each of your three full days you'd have to cover more than 625 miles. That's not a lot more than, but it is more than, the 600 miles professional long haul truckers are legally permitted to drive each day. And it means that for three days, the two of you are going to be pretty much cooped up together in the car with very little to do other than drive, drive, drive, only occasionally stopping for gas and fast food meals. Neither a fun nor safe way to travel. Even with four full days, you'll have to cover 550 miles a day. but that would leave you the opportunity to take a couple of one hour breaks each day to take a short hike, visit an historic site, or take some other mental/health alternative to just sitting.
If you choose to try to do it in 3½ days, I would strongly recommend that the first 'half' day be as long as you can possibly manage, indeed it should be at least 7 hours or so and cover at least 400 miles getting you just west of Des Moines. Then your next two stops would be Cheyenne WY and Wells NV. With four full days, your stops would be Lincoln/Omaha NE, Rawlins WY, and Carlin NV. Whichever schedule you choose to use, I suggest that you book accommodations ahead of time just so that you're not wasting time on the road looking for a place to spend the night, or get tempted to drive 'just one more exit' when you really need sleep far more than a few more miles.
AZBuck