Establishing relationships with the locals
This weekend I worked on some of of those activities. For the Montserrat trip, I sent an email to the head of the Montserrat Amateur Radio Society (MARS) indicating that our DXpedition team would like to join their organization. If you are thinking of going to some interesting, far away place, consider joining the local radio club. To me it seem like "good form" and "the right thing to do" to support local hams while you are guests in their part of the world. Plus, these folks could be a very helpful source of information. Establishing a healthy relationship could be very helpful for your efforts. I've also asked if they would like to join us for a cookout one night while we are on the island. I hope they'll join us!
I also wrote to the owner of the villas we're renting asking if he could help me finding options for getting to the island. There is a small airline that makes runs between Montserrat and the Antigua, but the baggage restrictions are fairly draconian and it would be nice to have another option. I had hoped to find a boat we could charter (the ferry service halted some time ago) but our host indicated there might be a chartered air service that should also be considered. That's the first I had heard of that!
Again, establish a relationship with people at your destination and, while being considerate about taking up their time, ask for some help and advice. The locals could be your best asset during planning.
There are lots of other loose ends that need to be tied up. We hope to do some portable operation while on the island and will need to procure some batteries (maybe car battery size) to power the radios on these jaunts. So, I asked our host if he had ideas on that issue. He did and I'll follow up.
The level of planning I'm trying to do for this trip might seem excessive to some but I believe it is best if I can answer all the important questions about how we will operate, log contacts, QSL, coordinate multiple transmitters, travel on the island, and communicate back home before we even step foot on the airplane. When I get down there I just want to relax and have fun knowing that nothing is left undone and nothing has been forgotten. That should be a good feeling--but there is lots of work to do in the mean time. I'm counting on the locals to help me.