I never really thought too much about the difficulties a photographer has during the course of taking pictures. There are so many considerations to take into account, from the uncontrollable weather, to the adversity in taking pictures of things that don't cooperate, or even people in natural environments. Taking pictures of natural settings is difficult too, as often natural settings aren't setup for the camera, but instead it is up to the photographer to setup the camera for these shots. I have several things I like photographing and each has a unique set of difficulties I have to work around.
Architecture - I really like the certain architectural designs and I try various methods to capture the essence of certain buildings. This is one of those particular objects that just does not come across easily in photographs. Think of a building like the Empire State Building in New York or even the Twin Towers in New York. If one has seen either of these buildings one knows that they don't impart their massiveness that they purveyed in person. This is the most difficult challenge I have found in architectural photography.
The other difficulty in architectural photography is trying to capture the shots to begin with. Buildings, as anyone knows, are freaking huge. Houses that have grand architecture are a little easier but skyscrapers and such are obscenely difficult to capture. I've pondered getting a helicopter ride or something of that sort to try some different views, but this is expensive and somewhat difficult to organize. Taking into account the difficulties of weather and other such things, trying to catch high viewpoints of buildings is very difficult.
Another attempt to resolve the angle is to take photos of buildings from other buildings, especially taller buildings. However this poses the security problem. How does one get permission to take photos from other buildings. Often it is as easy as just going inside the building a looking for an observation deck or something. In other buildings it means asking for permits, getting security clearance, and a hole host of other annoyances.
Trains, Buses, Airplanes, and Transportation - Trains in the United States haven't gone according to an accurate schedule in probably 40 years. Airplanes are a little easier, buses are too, and general transportation is a bit more difficult. Trying to capture railroad activity is difficult without a lot of patience and a good bit of monitoring. The other subjects are also quit a challenge, even when scheduling makes things a little easier.
...that's all I got for this entry so far...
I have tons of other photography frustration but I'm saving that for later... for now it's back to figuring out some good shooting projects. :D