I have organised many a successful holiday for groups of friends. Everybody who travels has a good time and suggests doing another one, so the organiser, forgetting momentarily all the headache that he went through starts planning the next journey.
This must start with locating somewhere that is nice yet cheap. This is not an easy task but if one starts early enough there is a good possibility of finding something. I had a little trick up my sleeve - I would get in touch with a printing firm in November or December and get the list of holidays for the forthcoming year, before any calendars had been printed. I would pick out the long weekends and start calling around and getting rates, take a straw poll amongst potential trippers and book, paying whatever advance was necessary.
Since we are booking three to six months ahead everyone is enthusiastic and confirms.
About a month before the date I start calling people to remind them and then the trouble starts. Some people have extra work in the office that they need to finish, other people are going abroad, some people can't come because its lent (April is always a problematic month), others have weddings, some people are not speaking to each other anymore, other people's parents object to them going alone.
When organising an outing, a rough transport plan is also at the back of ones mind, a few people with company cars (hence free fuel) providing the transport but with the drop outs, the transport plan will also be thrown into turmoil. One may have people but no transport or the converse.
All the problems do not come together, its starts gradually and builds up over the weeks until a few days before the journey the organiser is left with just a couple of people, which means a last minute round of frantic calling to try and find replacements.
The last time this happened was in 2007, when I was left with two or three people for a bungalow in Nuwara Eliya booked for eight. Thanks to the kindness of the owner, we managed to postpone the booking, which eventually had to be re-postponed once again before the trip finally took place in September. A couple of times I have ended up giving away bookings to other friends-bungalows are much in demand close to the dates booked so have not really suffered financially but its the frustration of having a great place but not enough people to go with.
Traveling in a group is fun and cheap - if a bungalow can be filled to capacity the cost per head works out quite cheap. I dislike hotels and these days they are far too expensive so a bungalow is the only viable option, the problem is in finding people who can make a commitment. A commitment for a holiday, that's not too much to ask for, is it?