There seem to be few instances of water leaks into the interior, so check the carpets and the trim for dampness, be on the lookout for musty odors indicating wet trim, and check that all the doors and the tailgate fit snugly and seal properly. A few issues with the seat heaters have also been reported as the Escalades age, so make sure they work; remember that all four seats are heated. A few have failed and burnt the seat, so check for this as well.
There are reports of a few 4x4 problems on 1999 and 2000 Cadillac Escalades, front-end differential failures sometimes being mentioned, in addition to the odd transfer case giving up the ghost. It is unclear whether this is due to the advanced age of all these first-gen Escalades or some other fault. Be that as it may, be sure that the differentials are quiet and replace the diff and transfer-case oil as a precaution - and as scheduled. As is the case with many old cars, suspension bushings, control arms, and tie rods wear out and should be replaced as they fail. Don't wait too long, or the car may develop handling problems. When the vehicle starts to wander, develop suspension clunks, pull to one side, or lose directional stability, have the suspension and steering systems inspected.
Although there was a recall for an entertainment system's bracket that could touch the fuel tank and cause a leak, that was not the last one of the fuel-tank problems. Quite a few owners of 2000 MY Escalades report fuel leaks due to cracks or other fuel-tank leaks. Make sure that there is no gas smell around an Escalade you're looking at that may point to a fuel leak.
These cars are all old by now, and although no special mention is made anywhere of particular problems with the 1999-2000 Cadillac Escalade's air-conditioning, blower-motor resistor, heater, or evaporator, the refrigerant may leak out over the years, and the odd heater blend-door may get stuck, so test the system thoroughly on a test drive. Any leaks that do occur seem neither chronic nor commonplace, so there are few problems with performing a standard AC recharge, and recalls for the 1999 or 2000 Cadillac Escalade's battery, alternator, or other electrical components were never necessary.
Other than the more common anti-theft and ABS issues mentioned earlier, there were also a few problems with the distributor on 1999 and 2000 Cadillac Escalades, so if starting is difficult or idling is rough, check the distributor and consider replacing the spark-plug wires as well. Other electrical issues with the bodywork and engine, such as problems with the brake lights, ECM, or BCM are rare on 1999 and 2000 Cadillac Escalades.