A couple of my kids had to fly to college. They always used Supershuttle. Always reliable and less stressful. Pay for the shuttle at move in, and then your son can see/ask other students about public transport, try it later.
Freshman moving into college for the first time with two large suitcases? I’d pay fur the $80 shuttle. Why the potential additional stress? His time and lack of frustration is worth it. If I would pick the $80 for myself, then I pick the $80 for my child.
If I couldn’t afford the $80 on top of the other miscellaneous costs that precedes sending a child to college, then of course, I’d choose the $6 but this doesn’t seem the case. The student can use the least expensive method on subsequent trips.
Had to chuckle here. After his first 2 visits to NYC my suburban raised kid could navigate the subway system pretty much anywhere (including outer boroughs) he was in middle school at the time. He has also managed other major cities (Chicago and Seattle) by himself while a HS student. He traveled back from europe alone at 17 and has since traveled alone there (he is now 19).
I think he has a GPS embedded in his body.
Read the OP’s post again. Student is traveling TO school from the airport. In that case I would let them figure out the public transit system. He is not in a rush to make a flight, he has time to make mistakes. If this was his flight home from school, first time, I would have him use a shuttle or Uber. (My 15yo D uses Uber frequently in Boston, I am very comfortable with that option. And she knows the how to navigate the T in Boston, but sometimes Uber is the better option). Too mush stress taking public transportation while trying to make a flight the first time, imo.
DS#1 opted one time to use public transportation (2 busses and a light rail). to get back to campus with his stuff. He was on the right bus but the new busdriver went the WRONG way, taking him way out of his way and causing him (before smartphones and google maps) to be dumped of in a not so great part of town to get another bus back to the right place. Never again. He then shared taxis, and once rode the free hotel shuttle to a hotel near campus 
BTW, been on those shuttle vans. Not sure “cushy” is the correct adjective.
Going to school at beginning of year - take the expensive shuttle. Going home for the holiday with 2 suitcases - take the expensive shuttle. Going back to school after holiday - schedule the flight to allow for extra time, take the inexpensive public transport, leave one suitcase at home.
DS flies back and forth to school all the time and takes the public transport option. BUT, he only travels with a backpack and 1 suitcase (and sometimes no suitcase if he is just home for a few days) and is a seasoned traveler (solo for both foreign and domestic travel many times). With two suitcases and the stress of move-in, etc. I would spring for the shuttle or Uber. Then public transportation for every trip after that.
2 suitcases? No question - pay the extra. It’s the choice I’d make for myself and certainly I’d gift it, at least on the first trip, to my child. When more experienced, other options are more acceptable.
I remember being a young woman just out of college and pretty broke. I’d been visiting my parents and my dad slipped me cab fare from the airport to my Chicago apartment just as I went to board the plane. My mother would have objected had she known - I was to be considered independent and off their “payroll”. Well, that plane was late - very late. I would not have had the cash myself to get a cab or limo and the public transport options to my apartment were not comfortable or particularly safe for a young woman struggling with luggage at that time of night. I’ve always been grateful to my dad for his loving, thoughtful gesture.
Granted, we have ATMs now for emergency cash needs and some cabs take credit cards, but I’ve always felt good about giving my kids a small emergency fund. If concerned about the mis-usage of the fund, it can be a loan.
They are, both by definition in the original post and in reality, quite cushy. Entire fleets of private vans, which are basically taxis, will pick you up at the airport and take you top your destination.
I would outline the alternatives and let the student choose.
It depends on his travel arrangements, too. Sometimes public transit works wonderfully, but not always.
I don’t know. As long as my kids were concentrating intensely on their studies, I felt their time was very valuable. I don’t know how to assign a dollar amount to making the most productive use of their student years. Of course, you could argue learning to use mass transit is also an important learning experience. That is different than making it about the dollar amount.
Will you be annoyed if I ask a different question? How does everyone feel about offering to pay for taxis back to campus, after going out with friends, if something unexpected comes up? Again, if a family can’t afford it, they just can’t. That’s that. End of discussion.
I encourage my daughters to use some form of public transport to get home after going out with friends, and I pay for it, if given the opportunity. I’ve never felt this “privilege” was abused by them.
I have always told my daughter if it is late and she feels public transportation is not safe at that hour - she should use her credit card and pay for the taxi for herself and her friends. I recently footed the bill for a taxi from an airport when a very delayed plane made the cheaper public transportation unsafe in my opinion (safety is always worth the money).
I agree that if the OP would take the shuttle and thinks it is worth it for him and that his time is money then why would he not agree to it for his child!
I recently had a conversation with my husband where we were discussing how when deciding on purchasing something for ourselves we will debate endlessly over the expense (even for something cheap like a $2 app), but if there is anything our daughter needs we will buy it for her without a second thought. I would probably take the cheap public transportation myself and have my daughter take the shuttle. I think a lot of this thinking is based upon my daughter not asking for much and thus not costing us much. So, if she wants something, it is our pleasure to give it to her.
DS’s “time is money” value is different from my “time is money” value. It’s not equivalent. Different inputs might lead to a different output in terms of a decision.
ETA: Obviously, his “time is money” value is lower than mine. Saving a half hour for me has a different value than saving a half hour for him.
I don’t know. Saving half an hour for my kids might sometimes have meant being the top scorer on an exam. Maybe not.
ETA: Of course being “top” scorer may not be a typical goal. It was my kids’ goal. They were accepted into their first choice, fully funded PhD programs. That has saved us oodles of money.
Everyone thinks their time is valuable. Is your time valuable during non work hours when you would otherwise just be relaxing? Why? I’m sure your kid could find better things to do too, or he could get their quick and pay video games!! I’m not sure time value is a good measure.
I think ride sharing us the way to go. Those vans hold a number of people and it can then be less than half the price. If you can afford that, that is my choice.
@alh Howzat? Sounds like a stretch. School hasn’t started yet.
Just in general terms. I find the time/value argument intriguing and think about it differently than you do.
If I could afford it, I would pay for the shuttle for starting school. Unless the student said that is a silly expense and he could handle it on his own.
When I was moving one kid in sophomore year, a group of athletic looking guys were chatting about their move-in. One was sad his parents hadn’t come that year. They had sent his older sister to ride with him in the car he would have on campus. She flew home. He felt neglected. That was unreasonable, but there it was. I felt bad for him.
However, junior year I didn’t move my own kid in. 
He flew on his own. But he took the shuttle.
I wouldn’t make the poor kid schlep 2 suitcases on public transit. If you can’t spring for a parent to help him move in, at least don’t put him on public transit with his bags in the aisle.
Does SuperShuttle work differently in whatever city he is in than other major cities? The shared van option where you don’t have to find others is available in DC (I have taken it) and LA (my kid does it all the time). Or is that the $80 option, and you could pay even more for a solo van ride?