When it comes to the Cadillac Escalade, there are certain model years to approach with caution and others that stand out for their reliability and performance. Generally, it's wise to exercise caution with earlier model years, particularly the first generation introduced in 1999, as they may have more mechanical issues and lack some of the modern features found in later versions. Additionally, the 2007 and 2015 model years have been noted for various problems, including transmission issues and electrical problems, respectively. On the other hand, the third generation, starting from 2007 and onwards, has generally been praised for its improved build quality and features, with many favoring the 2016 and 2017 models for their blend of performance, technology, and reliability. It's always a good idea to research specific model years thoroughly and consider factors such as maintenance history and vehicle condition before making a purchase decision.