Interesting. Well the two examples cited certainly illustrate what is IMHO an error - I don't really think the wording for that award is open to interpretation even though it is a bit clumsy**.
The thing to do is to leave it for now obviously, but as LWB says make an adjustment for next season - either correct the calculation to match the wording, or alter the wording to match reality, eg "1000km in at least 4 events including at least 1 300". The latter would involve a Regulation change. (Incidentally the "only rides up to 400" condition doesn't seem to be in the Regulation.)
** when it was set up, the idea of the R1000 was to be a sort of SR-lite - ie a 400,300,200,100 series (=1000). However at that time the Accessibility Police were strongly involved with defining the new awards, and wanted them to be attainable without any night-riding. Hence the compulsory 400 was ditched in favour of "100, 200, 300, plus other events to a total of 1,000 km".