I'm going to post anonymously, but even so, I'm afraid I have to disagree with how you're looking at this.
According to the article he made about $750k over four years at Box ($95k/yr salary + $350k in options total), but would have made nearly 60% more, or $1.2M, working for a more firmly established post-IPO tech company during the same time (say $160k/yr base salary + $40k/yr bonuses + $100k/yr in restricted stock).
Still wouldn't have been able to buy a Bay Area house (not sure why you suggest it could), but he would have had all of the other payouts you listed, with basically no downside risk at all.
Seems like pre-IPO companies like Box are increasingly a bad deal for the employees. I'm genuinely sorry you guys ended up getting the short end of that stick.