1. Travelling by loaded bicycle in hilly terrain having never toured before
2. In winter (but mild compared to my usual)
3. No training
4. Buying all gear in a foreign city, in about a week
5. No time for properly testing gear and getting used to the bike
6. Starting in Istanbul
7. Intending to ride clipless for the first time (after I get out of Istanbul traffic)
8. Wild camping near roads and populated areas for the first time