Absolute best crimpers are Certicrimp crimpers from AMP. Those generally start in the $300s and aren't found in a lot of places.
IMHO - best crimpers are the ones with locators such as the Molex HTR2445A (Sargent 3136CT). No holding the pin - push up tab, drop pin in hole, release tab. locator holds pin in proper place. Locator doubles as a wire stop to keep you from inserting wire too far, crimper then crimps both wire and insulation at same time. But these crimpers tend to run $100+. You can OFTEN find them on ebay at <$40 per pair.
The sub $50 crimpers -- this tends to be a Ford versus Chevy type issue. Lots to pick from - some suck ... some work quite well. But I don't use any in this category - I bought a full set of Molex crimpers off ebay.