Assuming the kart uses the modern (within the last 10 years) bearing carriers (not the triangular sandwich plates), you should never suffer from putting a sideways load on the bearings, so long as you tighten everything in the correct order. i.e:
1) Tighten carriers to hangers. 2) Tighten grub screws. 3) Tighten pinch bolts on carriers.
Doing things in this order allows everything to line itself up and ensures a free running axle.
Bearing seals should remain in place. Flush them through with WD40 or similar then spray with a proper PTFE lubricant as suggested by Brian P.
Chains should be cleaned in some old mixed fuel at the end of each day. Lightly lube the chain every session throughout the day.
How often you change bearings depends on the loads placed on them and the conditions they are run in. If you have lots of wet weather you'll probably have to replace them much sooner. Check for excessive play and replace if necessary. I replace them (along with rose joints, stub axle bearings etc) pretty regularly (certainly every season if you race once per month) as they contribute significantly to the overall predictability of the kart.
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