Crossfades definitely have a "sweet spot" in terms of cross fade length. Too short, it sounds more like artifact and too long: you listen to both songs at the same time which is often weird especially if they clash in time signature and key.
Most difficult tend to be songs that start or stop with a big bang or have a slow fade or fade out. An extreme example is for a slow start and big bang ending is Maurice Ravel's "Bolero".
So difficult song pairs would have
- Clashing keys (e.g. half step apart) especially if they also have long chords in the intro and outro
- Clashing timing (speed difference by maybe 10%-20%)
- Slow fade out into a slow fade in (ends up with a big hole in the middle)
- Big bang start (starting chord gets cut off)
- Big bang end (ending chord gets cut off)
- Any combination of the above
Crossfades are generally not a good idea and I avoid them whenever possible.