I've thought a lot lately about choosing frugality when it's off in the future vs. when you're in the middle of a situation where throwing money at the problem can make it go away.
Basically, do you pay for seats on the plane ahead of time?
We recently flew on a low-cost budget airline that charges extra for everything from carry-on bags (yes, carry-on!) to soda onboard the aircraft. Of course, choosing your own seat cost extra as well. I'm still getting used to traveling with other people than just myself, so on the first leg of the flight, I did what I would normally do - save money by not choosing seats ahead of time. This meant that I was stressed out about whether or not we'd all get to sit together right up until we checked in at the airport - and then my stress level skyrocketed when the agent looked worried as she tried to book our seats. She was able to get us in a row together (two adults, one kid, and one baby in arms) but it wasn't a sure thing.
Now, I will argue all day that when you buy tickets at the same time on the same credit card OBVIOUSLY you should get those seats together, but that's not how life in the real world works apparently. For the flight back, I paid $15 to make sure that we got a row together so I could avoid the stress of not knowing or of asking people to move so that we could sit together. Actually, I wasn't too stressed out about asking people to move (one look at our babies and people would probably volunteer to sit somewhere else!) but it occurred to me that if someone else had paid to select a seat and then had to move because of my wanting to save money, I would have veered from frugal to miserly, and that's not a line I want to cross.
Paying for it as a separate expense still irked me, so I tried to think of it as just rolling it into the cost of the plane tickets - they were still so much cheaper than another airline that would have offered confirmed seating for free. Being in the middle of the situation rather than just imagining it down the road made it a lot easier to throw money at the problem to fix it. I'm sure I do this without thinking all the time, and it's a slippery slope (buying the candy bar to stop your kid's tantrum is effectively the same thing) but sometimes I know I am just too cheap for my own good, and I'm glad I coughed up the money to relieve some stress during our trip.