Is it Worth Building a SMALL Contest/DX Station?

$25 Grand, that is puny by contest super station standards. They spend $25 grand on linear amplifiers. One of their towers probably approaches 6 figures and many super stations have a "farm" of them. As for "breaking a pileup" I doubt very much 20 watts is breaking any pileup. What is happening is that your signal is audible during a lull in activity, because I assure you no one can hear you beneath all the KW super stations. I run 50 watts CW and 100 watts SSB when the Alpha 86 isn't turned on. I have lost count of the times turning on the linear immediately broke through the pile up. If you persevere, you will on occasion, find a sweet spot of timing when all the signals competing with yours temporarily fall silent. You can't violate the laws of physics just by wishful thinking
AF4RK

 

Depends on what you find enjoyable. I enjoy making over 1,000 QSO's in a weekend, so yes a special station is required. Contest conditions are very competitive. You won't make any contacts with compromise antennas. If you listen tot he HF ham bands on a regular basis, you know very well that most HF activity is contest related or special event related.
AF4RK