The piston doesn't look too bad really. No pics of the front edge?
Can you also confirm how you measured the end gap on the rings? It's not often to see them so far out of spec. I ran a set of 250cc rings for 120 hard hours once and had noticeable decline in power which only measured 0.9mm.
On the other hand a mate drowned his te300 and continued running it with a silted engine and it ran until it ran out of compression. The kick starter turned over like the plug was out of the head.. and when we pulled it down the rings were so flogged out that they would falls straight through the cylinder.
The transmission fill point is up above the countershaft sprocket. It's same size allen key as the drain, and the fill hole is about as big too. Most of us have a bit of tubing attached to a funnel to feed it in. Some use a sealed bottle to help force the fluid in a bit quicker. 900ml-1L does the trick.
You mentioned a faulty kill switch? Does this mean the bike has been running poorly; ie cutting out, spluttering, hesitating, etc.. or is it simply under powered? I agree with above that if it's running poorly as well as lacking go that it'd be worth double checking other faults. You could also consider measuring the trans oil you dropped out to see if its in the range as above.
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