Why is a high-Q circuit difficult to match?
For high Q systems, the impedance of the circuit changes very rapidly when you change the frequency. The circuit driving the high-Q system is designed for a specific impedance, and if the impedance is different performance will suffer. In an antenna, it means that much energy sent to it is actually reflected back to the amplifier, instead of being converted into radio waves.

Therefore the impedance of the amplifier needs to be carefully matched to the impedance of the antenna for high-Q systems, at the frequency being transmitted. 

Special measuring equipment is needed to determine how much energy is reflected. Also, while making the adjustment the impedance is often affected by the proximity of your hand or tool, meaning you will have to make small changes and observe the results.

Also it may not be clear which part of the system needs to be tuned. Especially with microwaves, every part of the system transporting the wave may need to be tuned.