I'm not the person you're replying to, but I do have something to say about this.
Your situation is a bit different in that you need to be able to get from Portland to SF and back in a single day. Some people, myself included, don't have that restriction and value the journey as much as we value the destination. Personally, I absolutely LOVE long road trips. Seeing sites, eating at cozy roadside diners, listening to super loud music and sleeping in my car are all things I look forward to.
I really hope Microsoft doesn't fly their candidates with United anymore. A couple of big companies cancelling their corporate contracts might give them a reality check.
Have even cracked a joke or two with TSA agents & gotten a "Welcome to America, enjoy your holiday" at LAX.
I don't get ever get bumped from flights and I get pulled out for "random" searches on average of 1 times per year for the past 5 years.
Again, all anecdotal, but I'm the definition of the guy who should hate the airport. I only just dislike it.
I frequently go from Portland to San Jose and back in the same day- I get meetings done and am home in time to put my kids to bed. I also just generally fly pretty frequently. I've got an Arab name and my dad comes from 'one of those countries'. I lived in that country for a few years as a child, and I've visited a few of 'those countries' in the last three or for years. I've literally not been hassled beyond the occasional extended screening XXXX on my boarding pass- like, maybe 2 times in the last three years. I have been bumped from a flight zero times in my entire life.
150 years go if you wanted to travel from California to Oregon you'd be going up the Applegate Trail and the TSA wouldn't even be top 10 annoyances along the way for travel. I say that semi in jest, nor am I endorsing the TSA in anyway shape or form. But frankly, if you're worried about getting bumped or hassled by the TSA I think you're worried about the wrong thing or you've got a very peaceful life that hasn't got many things to worry about.
I'm not saying commercial air travel isn't without its issues, it's generally just kind of annyoying to stand in lines, stand in more lines, then get crammed into a metal tube with my knees smashed against the seat in front me. It's just that the likelihood of some catastrophe (drunk, mental issues, etc.) that isn't self imposed is quite low.
My n=1 anecdote is just that, but I would wager I'm more likely to be hassled or be hit by airline failure given all of my variables AND the sheer number of flights I take compared to the average person. Yet hear am I saying the airlines and TSA aren't really THAT bad. Talk about playing devil's advocate.