Would You Rather?

Would you rather plan a trip for many months, be excited about the upcoming departure and then have the trip revoked due to another's mistake or plan a trip at the last minute, throw the details together and be one step away from boarding the airplane but not be able to go due to your own blunder?
I ask this because the latter sucks and I want to tell you why. James has planned a trip to Europe with his friend Baron for the last couple of days. It was a thrown together trip, but not near as bad as the tale I'm about to tell you. During a few minor changes to the trip, Baron flaked out and came to America early (he lives in France). In fact, he was in America before James ever left the country. This left James backpacking for seven days in Europe (cool), alone (not so cool).
This is where I come into the picture. At 12:13 p.m. on Monday, December 6 I was telephoned. Sadly, I was subbing and did not receive the phone call, or the subsequent nine phone calls, until 3:18 p.m. I was asked by James if I was interested in leaving for Europe tomorrow for a week. I was a little apprehensive at first, however when I hung up the phone I was extremely interested. The following is the order of events that occurred:

3:19 p.m. - James called American Airlines about a ticket he discovered on the Internet for $695. This was an Internet price only and could not be reached due to my immediate departure.
3:26 p.m. - James searched other outlets for a ticket and I rushed home to change and meet James and my mom at their office.
3:41 p.m. - I arrive to bad news about the ticket. The cheapest available price is $1,800. I can't afford that and my mom was not willing to front the money for me. I don't blame her. I'm a college graduate with no real job or ambition. I wouldn't give me the money either.
3:56 p.m. - My mom called a friend of hers who knows a guy that is in the cheap airline travel business. After forty minutes on the phone (32 minutes of it being on hold with Christmas music... Do they know it's Christmas?), this door was closed.
4:46 p.m. - I am given permission to use my mom's American Express points to get a cheap ticket.
4:46:15 p.m. - James and I are on our way to my mom's house to find her American Express bill and investigate this prospect.
5:59 p.m. - I have a ticket booked and waiting for me at DFW Airport.

All I have to do now is get my mom to call American Express and transfer her points to Delta and find my passport. No problem. Oh wait, problem. My mom won't transfer the points you ask. No, I can't find my passport. After searching the obvious places like folders and boxes I move on to less obvious places.
Something you need to understand about me is I live in a fantasy world. In my mind, I am James Bond and the villain is always after me. I am in the middle of a spy world and must hide important documents (like a passport) from men who might break into my home, search my room and steal the for-your-eyes-only documents.
I looked behind pictures in picture frames, in-between books (both a book's pages and two books together), in board game boxes and throughout any other item that I could possibly hide a passport in. If I wasn't a freak about things like this, I would have found my passport and I would be on a plane for Europe right now.
By 10:51 p.m. I had given up the search and had to decide whether I wanted to risk sitting in the main office of the passport bureau and try to process a passport in four hours or give up on the trip and try again some other time. Needless to say, at 10:56 p.m. I chose to call and cancel the ticket. It's 6:35 p.m. on Tuesday, December 7 and I'm sitting at my mom's computer typing about the what if.
So you tell me, would you rather...