Actually what’s missing is the OP 
My kids’ safety is always number one…if it’s late at night and they don’t feel safe, then yes, I would pay for the taxi. In fact, my daughter is currently studying abroad in a big city. She mentioned that she went out with friends but wanted to come home earlier than the others. Fortunately, she did find someone to walk home with. But when I heard that story I told her, if that ever happens again and you are alone, get a taxi…I’ll pay!
As for the original question…First off, personally, I would go with the student…freshman move-in? I’m not missing that! But that aside, that’s a lot of stuff to lug and first time arriving…I’d make it as easy as possible and splurge. This is especially true if he’s the type that has never navigated public transit before.
What does Susie Orman say about this?
"Two suitcases and a backpack on public transit would be a real pain, both for the student and others on the public transit."
This. Emphasis added by me. Fine on a train like the our Sound Transit light rail
which has designated areas for luggage and bikes, not so fine on a crowded Metro bus wich requires getting up a flight of steps to get onboard (I’m using local examples).
Some public transit, like “TheBus” on Oahu, do NOT ALLOW suitcases to be brought aboard. That leaves the student in quite a predicament and is a pretty harsh way to begin college. Suitcases really are difficult to lug up and down steps, and even where there are escalators and elevators, they may be out of service or tough to navigate with luggage.
I can share 2 personal experiences with luggage on public transport within the last 6 months. First, I was the one making the wrong decision. First time to Berlin, guidebooks recommended public bus from airport, but failed to mention that this wasn’t a dedicated airport to city-center line, it was a standard commuter bus. I felt so bad with my single, 18 inch wheeled carry-on. Despite all my efforts, even this small piece of luggage created problems for those heading to work on what became a crowded, AM rush hour bus as soon as we left Tegel.
Last month, I was the one almost injured as a woman came toppling down the escalator having fallen over her 22 inch roll aboard on the way to the subway entrance. We both fell to the ground, or more precisely, fell down the escalator and were carried back to the ground escalator entrance level. Fortunately, no injuries.
My response to 2 suitcases plus backpack - unless this line is absolutely dedicated to travelers only, be considerate of others. I also agree with those who have questioned the “character building” aspect of taking on public transport when loaded down with luggage. It simply strikes me as cheap and, lacking any possible other unstated considerations, seems unfeeling on the part of the parent to expect a difficult public transport jouney on this once in a life time Freshman drop-off.
Exactly. Luggage on the train from Heathrow to London? Check! On LIRR? No way. Too crowed already!
Maybe OP isn’t responding because he’s off moving his freshman into college?
Do let us know what you decided.
We rode the train from Heathrow to London with baggage…with no problem.
This is an 18 year old. My new rule of thumb: lots of luggage, take the shuttle. Arriving very late, shuttle.
I’d give up a dinner out for the safety of my son, or me.
@alh: Your child would actually tell you if something comes up? My kid went to a party at a college which has a relationship with his and, he told me months later, wound up walking an incredible length of time toward home in the night with another student. Neither of them making some of the more convenient, and well-traveled choices their peers made.
When they started college, I talked their ears off about my safety concerns and fears, exploring all the various scenarios I could imagine and told them I would reimburse for taxis when needed with no questions asked. I asked them to please do it for me. And sometimes they told me they needed X amount because they had taken me up on that offer. I doubt it was a dozen times total for all sons. If they had abused it, I would have had to reconsider.
One son, while in graduate school, called and asked for reimbursement for airport transport. He had been visiting and staying with friends in a city and had a flight home which required him to travel to the airport after midnight. His friends were divided on whether it was safe to use the subway at that time of night. He opted for a SHUTTLE, which picked him up from the apartment. He told me that wasn’t in his budget, but he remembered I was always going to pay for safe transport and so he based his decision on that. I happily paid.
@thumper1 …thats why I said “check”. Those trains are built for that. The commuter rails in NY have NO space for luggage. When people get on with luggage it is frustrating for the “commuters” the rail was made to move…
Metro North out of and into NYC has really nice luggage racks on their trains. No problem.
Not! Only a small bag will fit up there and people get on with those big rolling bags.i ride it daily…no room!
Regardless, Metro-North does not go to Jamaica Station 
indeed. not even close!
http://www.thebus.org/howtoride/RulesReg.asp#Baggage%20Rules lists the baggage rules for The Bus. The maximum size for the allowed “Medium-sized brief case, duffle bag, or small metal bag caddy on wheels” happens to be the same as many airlines’ carry-on bag maximum size.
However, when the public transit system in question is a train with a stop in the airport, it is not a surprise to see people bringing large suitcases in the train.
All the talk about how difficult or restrictive some public transportation systems are, seemed rather extraneous. Facilities and policies are easily checked by Internet these days. Who would try to take a large backpack or additional luggage on board a bus where it was prohibited or who would expect someone else to do it?
I’m also struck by how many people think carrying a backpack and two suitcases is a hardship.
I think it was mentioned somewhere in the thread that the parents pay for the big-ticket items and expect the students to budget and cover all the small things. Wouldn’t giving them money, in any amount, circumvent this policy? Besides, what student doesn’t have $80 in their account?
My son, who covers the small things, often asks me for advice on whether it’s worthwhile to spend money on something or not. Just yesterday, he asked for my advice on buying a table for his apartment. The problem was that the delivery charge was almost as much as the cost of the table itself. We discussed ways in which he might be able to get something similar without paying a big delivery charge.
In the discussion above, I think there are a couple of different issues. One is whether it would be worth it, in general, to spend money on a shuttle when there is public transit available. It seems to me that many of us think that it might be worth it, if you can afford it, depending on the specifics. The other issue is the extent to which we, as parents, want to fund extras and luxuries for our kids. Here, putting aside for the moment the issue of whether you can afford it or not, I think it depends a lot on what your kid is like. There are kids who have to be urged to take a taxi at midnight, because they have internalized frugality. If you have a kid like this, you may find yourself saying, “Take a taxi, I’ll pay for it.” There are others who need periodic reminders that things actually cost money. To these kids, you will find yourself saying, “What’s this $9 Starbucks charge on my credit card?” I don’t think this is entirely upbringing, because these kids can coexist in the same family.