Tailwheel Issues
Very much a 'type' issue and how good your type checker is.
However there are a couple or things you can do to be ahead of the system.
Know how 'your' actual tail wheel/skid should work.
In the case of a TW there are several types which run from fully castoring to lockable, and the common spring connected types with a self center bias**.
In the case of a skid some are fixed and some steerable.
If you understand the way the TW 'should' work it helps.
X winds are more of an issue with a TW so be aware of this and the limitations.
Grass surfaces are a bit more TW friendly, but if you are faced with a tarmac situation be very aware of an out of wind situation and/or a zero wind as any departure from the norm will be more 'lively' and faster. Be Aware, Anticipate, and have sensible limits whilst you build EXPERIENCE which is the real teacher.
** These are common on lots of TW machines, but need to be correctly set up as they involve springs and 'break out' systems. your local engineer can explain how it works, but make sure the springs are connected when its wheeled out.