He said daytime and a relatively safe area. However, some us of had first years who could navigate hazardous urban environments easily and some of us had first years who inevitably lost their keys, their wallets, got pickpocketed, etc., so minimizing that risk might be worth something to us. The particular kid matters as much as the environment. imho. ymmv.
and yes, eventually they learn, but some just take a while longer than others…
I have no way to judge what is appropriate in this case.
If affordable to your family, I would go for the shuttle for this first trip with all the luggage and use the cheaper alternative for subsequent trips home. I think it would be helpful to arrive for the first day of college as fresh and full of energy as possible.
Time of day is a real issue. We did a practice run of taking the train into the city and connecting to the subway system from my daughter’s college when we visited in July. If it were daytime, that would be a good way for her to get to the airport, though probably an hour longer in transit. However, if she has to catch a really early flight to make an overseas connection as she is apt to do come Christmas vacation, then we will pay for the shuttle service that will pick her up at the dorm and drop her at her terminal at the airport. It is still very dark early in the morning and the train/subway option might not even be going at that very early time of day.
OP - I have a question for you.
Lets say you are a man travelling on business and you are transferring from the airport to a hotel. You have a briefcase and two suitcases. What would you do? Public transportation or the shuttle?
DH would pick the shuttle. We would also pick it for our son. It’s not worth the savings for the “potential” problems with the other options. Especially with a freshman.
I’d pick the shuttle. But, my time is worth money.
You know, you’re not locked into an option forever. Why not do the shuttle the first time - the kid will be anxious, will have enough going on, will be nervous / excited, etc - and then in the future for trips back and forth, you can have him do public transportation or coordinate sharing rides with other students.
Is this a “I can’t spend the money” issue or a more philosophical “I don’t want kid to get spoiled” issue or what?.
With two suitcases and a backpack use the shuttle - with just a carryon use cheaper public transportation. Very hard to maneuver luggage on light rail and other public transportation. I know as I got my suitcase stuck in a turnstile on the Paris Metro ( had a Paris transit worker cursing me out in French as we tried to get it free).
Think how much money you’re saving by having your son travel alone to school.
One of my sons started as a 15 year old child doing an airport to boarding school transfer that involves 5 rail links, plus a cab ride. He does this solo w a backpack & luggage.
So I think 2 cushy shuttle vans and light rail should be a piece of cake for an 18 year old adult male.
@Pizzagirl Once the kid passes through the homestead portals, they’re gonna’ do what they’re gonna’ do. Personally, as students, my wife and I agree we’d use the money saving option. $74 is some nice meals out, three days of dorm food, a good date, the surprise textbook you have to have, your half of a refrigerator, etc., etc.
I think it all depends on what your son says he thinks he can handle, and what you’re comfortable with.
Sounds like a sojourn my oldest made just last year. I thought I’d mapped out everything for him, including where the neighborhood landmarks he would be passing were, and that would save him the heartache I was going to endure knowing he was on his own. He told me at the end of this summer that he walked in circles for about 15 minutes, which frustrated him, but then he was fine. (He’d already traveled on the two rails after his arrival at the airport by the time he was on foot and spinning, and near enough to know he was almost there,
(He had one bag less than your son will, and was truly a kind of sheltered kid to begin with, but he handled it as though he had hair on his chest. 
I wonder why this $75 has attained such significance (as compared to the perhaps 500 times this amount being spent for one year of college).
The big reason I favor rail is that it’s often the the less stressful option when dealing w major traffic congestion around a metropolitan area.
@rosered55 I think because the tuition costs what it costs and there is a reasonable option for the transportation.
In fairness, people can afford to be paying $60,000 (or whatever) for a year of college precisely because they do sweat the $75 here and there. I can understand the desire to save the money.
"One of my sons started as a 15 year old child doing an airport to boarding school transfer that involves 5 rail links, plus a cab ride. He does this solo w a backpack & luggage.
So I think 2 cushy shuttle vans and light rail should be a piece of cake for an 18 year old adult male."
Your son is FAR more well-traveled than the average 18 yo boy!
I miscounted. DS’s land transfer is only 4 rail links, not 5.
Some people can easily navigate a multi-segment mass transit trip. Others will get easily confused on just the first segment.
Among 18-year-olds, the free range city kid who takes the local buses and trains all over the city would probably better be able to handle the multi-segment mass transit trip than a helicopter-parented suburban kid who has never gone inside a bus or train.
LOL, my daughter can’t drive worth *****, but she can figure out any complex subway map (i.e., Tokyo, London) in a split second, figure out a bus system, or feel comfortable calling/hailing a cab. It truly is a matter of perspective.
I missed it, is S comfortable with public transportation?
I grew up in an area without public transportation. Zip, zero, nada. No buses, no trains, no cabs (is that considered public transit?). I’ve ridden a train maybe 5 times in my life- all when I was really little and visiting family in Chicago. Don’t remember any of it. I never rode on a bus until college. I would get the shuttle especially with luggage and going to a place I’m not yet very familiar with.
If, OTOH, he’s a seasoned traveler then it might not be a big deal.
Moving into college for the first time can be very stressful. I’m pretty tight with my money but I think less stress is definitely worth the extra $70+.