The packages with the film were almost always "beaten up" to some extent. Usually, the beating was minor, but a couple of times the enclosing box had severe structural damage. One package I sent home from Australia had been crushed enough that it had a large hole torn into it. Fortunately, nothing was lost, as I had the foresight to put some small items into a small box, before placing it into the large box. I always kept the film in the original sturdy 20-sheet quickload boxes, and the film always arrived intact.
Packages sent by courier service were usually in very good condition.
The only pre-booked travel I had was for the long international flights.
My rough itinerary was made with ideas of how I would travel between locations, based on information from guidebooks (ie. "there is a train from city X to city Y; busses frequently depart from the station in city Y to village Z."). But I would change these plans on the fly as my situation changed (ie. I wanted to stay longer in one location, or cut out some other place). For example, in Vietnam I stayed longer around Hue, and flew to Saigon rather than take three days with ground transport.
I usually tried to make sure I had my transportation arranged a day in advance, such as buying bus or train ticket. Sometimes, it took an extra day because the transport was already full, the schedule had changed, etc.
Building itineraries and keeping schedules depends a lot on your personal goals and temperament. I tried to strike a balance between working to an itinerary, in order to see a broad range of locations, and "going with the flow" once I was at a location, in order not to be so tied to a schedule that I failed to "experience" a location. The best way to achieve this is to build in flexibility and "slack time" to your itinerary so you can adjust; you should also be willing to cut sections completely out of your itinerary, as necessary. Based on my experience, I recommend writing up an itinerary based on research for a trip that interests you, and then either doubling the amount of time, or cutting half of the itinerary. Seriously!
I will also re-iterate that large format photography was a principle goal of my travelling, and that, with proper planning, resources, and time, it can be done. I would also recommend that you schedule in time to "be a tourist", and partake of local culture and entertainment with no thought to photography, so that you finish the trip with more than just a collection of great photographs!
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