How about pre trip, during trip, and post trip, all in the same trip.
This August, first off, I hurt my right foot. Could barely walk on it, mad painful. We leave for Disney at 3:00 am from NY. By 7:00 am we are in Maryland on the beltway heading for DC when I hit a pot hole with the car, and it starts pulling hard to the right. I pull over, and discover that I've broken something in the right front suspension.
Turns out to be the steering knuckle. By the time
AAA gets a new knuckle, and gets the car back together, I'm out a thousand dollars, and it is nearly 12:00 the NEXT day. While waiting in Glen Burnie Maryland for the car to be fixed, my wife passed out pretty early in the hotel, so I took the son out for a walk to keep him occupied and out of her hair. During said walk, I fell into a hole, with the sore foot, and managed to bang up the other foot pretty good. Had my 10 year old son not grabbed my arm, and pulled me, I think my head would have been taken off by a passing delivery truck that I nearly fell out in the road in front of.
We forge on, and I drive from Maryland straight through to Orlando, arriving at 2:00 am. I'm pretty exhausted, and my foot hurts more than ever, but we made it. Next morning, we go check in at POR, and head off to DTD. DS and I go to Quest where I manage to lose my sun glasses. Of course, no one ever turned them in.
Toward the end of our first week, my foot is finally starting to feel better. Our first day off from the parks, we are supposed to be going to Typhoon Lagoon, playing a round of mini golf, and ending the day at DTD with dinner at the Rainforest Cafe'. We decide to put off Typhoon lagoon since the wife and have both gotten sick as sick can be. We head out to Wal Mart to get medicine, and fill the gas tank. Once the tank is full, I go to start the car, and it won't start. After going through everything that I could possibly fix on my own, I finally come to the conclusion that the fuel pump has taken a dump, and call AAA again. 4 hours later I finally get a tow truck to take me over to the AAA at Disney. They drive us back to our resort. By this time, it is 8:00 at night, the whole day was a wash, we did nothing except take our medicine, and go back to bed.
For about two days, I had a killer sore throat, then one full day of sneezing non stop, followed by a nasty cough that lasted the remainder of the trip.
We went to the villains party at DHS and got caught outside for nearly 40 minutes in a torrential downpour. Unbelievably, they wouldn't let us in the park to take cover in a building. By the time the rain was over, I was wet in places that don't even get wet when I am swimming.
At some point, I managed to lose my 2nd (backup) pair of sun glasses. My wife also lost hers, and our can of sun screen, none of which turned up at lost and found.
The repair of the fuel pump cost us another thousand dollars. At this point, money was getting pretty tight. Due to being sick, and sleeping in, we missed our opportunities to use FP+ on Toy Story (never rode it), and Rock N Roller Coaster (also never rode it).
The rest of our stay in Disney went pretty smoothly, though for the first time in for ever, I didn't book bounceback, because I wasn't sure if I could afford the two hundred dollar down payment after all the car repairs.
On the way home, my mother calls me, and tells me that our dog died. That kinda stunk, but we pretty much knew it was coming, just not exactly when. Then, the next day she tells me "I think there might be something wrong with the refrigerator." I'll make this part short, there went another twelve hundred bucks.
I think that pretty much takes the cake for a disastrous trip. Somehow, even through all of that, we managed to have a good time!!!