Great question!
While there are SO many things that I love about crossdressing, unfortunately, there are a few things that I do hate:
1. The disappointment of trying on a new dress that I'm totally excited to wear, only to find out that it doesn't fit!
2. Carefully putting on pantyhose, only to get a tear or run, moments later.
3. Getting psyched for a major crossdressing session and then learn that a repairman or other vendor is coming over to the house.
4. Changing back into yucky, uncomfortable guy clothes!