With all the added context, I’m more willing to say go for it. Not a trivial amount, but if it doesn’t create a problem for you to pay it and you have several reasons for wanting to do it, and doesn’t make anything weird, not much of an issue.
I had to Google that. I wish I didn’t!
I’ve known Anthony and Stuart for a long time. They’re important to me. And it’s always better to do things with other people than by yourself.
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I voted Nah because Naw wasn’t an option 
Seriously Matt! You’re already a pampered pet and want to turn your pals into one too!? 
An economy seat on a flight achieves the same outcome as a posh seat. Upgrading won’t make the flight get there any earlier. I definitely think there are better ‘experiences’ to spend your money on.
That said, if I was travelling with a friend who really really wanted to upgrade me, I would be delighted!!
When travelling before with friends, I’ve split the cost without telling them. I’d tell them that “I can upgrade your tickets to premium for only $250, I already did mine - if you can afford it I’d love to have you up with me”. They never knew the real price was $500, but I could afford half the upgrade (and not the full amount). It worked for everybody, as they went with the cheaper price.
I voted ‘Nah’ above, but after reading the thread, it sounds like it would not only make their trip better, but yours as well. Maybe you can meet in the middle, but if not, I’d do it as the surprise as long as I could find the money.
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This might be the killer argument, actually.
WAT is awesome, but expensive. A real luxury. They have no idea what they’re missing. They might think KS is awesome. They don’t know any better. I do. But I can put up with crappy KS, I suppose.
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Have you already done WAT? If it’s their first time I wouldn’t bother- they will be happy enough with KS. I can see your point though if you haven’t done it before and want to get it done this trip…
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I would upgrade the flight and not even mention it to them. Let it be a surprise at the airport. For first timers I would honestly not dedicate that much time to a tour like WAT, even if it is amazing.
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Yes. Twice.
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i understand it’s a special surprise to do wat. would it be an option to ask them if they want to do wat as a special add-on that they cover? if it’s really not about the money at all (for either) and you’re wholly comfortable being kind and generous, ignore this question. you know you and your friends best. i’d, for sure, be grateful if a friend was considering me as much as you are with your friends.
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Speaking as someone who used to like flying but doesn’t anymore, good seats make all the difference. Especially on the way to somewhere. If I’m tired or had a bad flight it really affects my mood for the first 24 hours.
Don’t know if they are that type of people, but if they are — and if their mood the first day or two will affect your own enjoyment — might be a reason to upgrade.
PS I have flown with my family when my husband had status and we did not. The rest of us could not go in the fancy line with him, he had to bump down to the cheap line to stay with us. YMMV.
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I’ve made my decision. Thanks to everyone for their input.
I’ve upgraded their flights. The only argument against doing so was cost. There were many reasons to upgrade but the final clincher was that it just felt wrong to start the vacation in two different parts of the plane. The clincher just before that clincher was this:
As for the WAT, my view is that if we do it (and it is an “if” now) we all pay our own way. I don’t need to do it again. They don’t need to do it at all. Unless they want to. Also:
That’s a good point.
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You are an awesome friend 
I hope it’s a great experience for you all!
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I remember when you said that about your first trip to Orlando…
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Shush.
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It is still true! It’s just that Matt keeps picking a different person’s lifetime each trip!
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Either that, or this is just one big long trip with breaks in between…
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In that case, he takes his “rest days” seriously!
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I’m not sure I would do it, but I understand the impulse.
Me on a normal day:
Me at Disney:
P.S. Fa la la
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Have you considered moving to FL? Think of how much you’d save on airfare this year. You’ve already proven you can work from anywhere. 
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Side idea: a self-inflatable Thermarest camp seat does wonders for me on flights (and longer commutes). One to sit on and one for the lower back. Deflates and rolls up nice and tight afterwards.
I like premium economy for the extra legroom but the seats themselves in domestic coach are often the same as regular economy.