I'm on a 3rd generation family that I have been playing for about a month off of a save. As mentioned above KW does not lend itself to lasting a long time it tends to get a little buggy so using the above steps has helped improve my game with KW installed lasting longer. These little steps help make it run with multiple mods. I go about 3 hours with at least 5 saves then exit out the game and clean my latest save then reload. Also, use Save As and save your game at higher intervals than you normally would. Another recommendation since I'm heavily modded and run KW is to use Kuree's Save Cleaner. If they conflict take out KW and restore your save. Add the Career Mod and see how it goes for a bit. I would recommend making a back up copy of your game before installing KW. Register and Dresser might have little conflict but I have been using them as well as Story Progression but I will tell you your game can get very heavy and crash if using 'EA worlds' I play in a custom empty world so I can build up my own population. I have Homemaker and Homeschooling and they actually work well with the mod. The only conflict that I know of at this time is the anything with the Education related careers. I have the Career Mod installed as well as KW.
