I prefer driving as well, and even though we have a lot of direct flights from MSP, I find that security, delays, car rental, and so on worth nearly 3 hours or nearly 200 miles of road time on the Interstate. My limit, though, is about 500 miles because distances beyond that are just too time consuming for driving. I did have a trip to Springfield, IL, though which ended up being longer flying than driving would have been due to a cancelled flight and getting re-routed via Chicago.
The upside even if driving is long is you can take stuff with you -- food, full-size monitor, a decent electric kettle, cooler, etc. All that makes a week at a budget hotel much more bearable, especially when you're working 12 hour days. I've worked a couple of projects where I literally didn't need to leave the hotel for 2 days (on one of those trips the manager called me on day 2 asking if everything was OK -- she explained they get edgy when guests at this location don't leave the room for a couple of days as it makes them think of crime/drugs).
From a rights perspective, though, I think it's a mixed bag. The whole TSA experience is like visiting a prison, but I've kind of gotten to the point where I think they don't give a shit about anything but potentially violent people and no longer have the cop's what-can-I-bust-you-for-today mindset.
And in your car, with out of state license plates? You're basically an engraved invitation for a moving violation and an intensive search, and god forbid the cop that pulls you over is anything other than a major city squad or a state trooper. The former don't generally bother with anything but egregious traffic violations and the latter the same, provided your car is late model and in decent shape.
But small-town cops and county sheriff deputies can be real assholes to out of state cars. They are hot shit in their jurisdiction, shitkicker ex-football bullies making $20k/year and just convinced that someone from out of state is carrying mary-wanna and they just love to offer you a deal -- let me search your trunk, or you can have a stay in the county lockup, eat a moving violation, impound fees and lose 48 hours of your life.