I have collected various things for probably 45 years. Market psychology applies here probably more than the Stock Market. If they are not great smokers, strike while the iron is hot. If they are great smokers, you'll kick yourself for the rest of your life. Now, I haven't collected pipes long enough to know what might be guaranteed to go up, or even double or triple in value, but I will share an old trick for those who might not have considered it. If you KNOW am item will double or triple in value, and you definitely want to keep one for years, buy at least 2. When it doubles, or even triples in value, sell one. Now you have one that was essentially free!