I pressure check the tires before every trip. I also do a quick walk around when fueling or stopped for some reason. Put your finger on the wheel near the bearing, it should be cool to slightly warm. Repack the bearings every one to two years, depending on how often the trailer moves. If it sits a lot, every year. If you use it a couple of times a month, every month, every 2 years should be enough. When you check the tires, also look at the tread for any separation and the sidewall for any "bubbling". Mostly, do what you can within reason, hit the road knowing that you will have your moments, adjust attitude accordingly and enjoy the thing!