Getting the 2-stroke oil to mix well would be my concern with adding AFTER filling. While non-vegetable (eg castor) 2-stroke oil is fully miscible with diesel, it could take a long time for the 2-stroke oil to mix well without agitation or stirring, especially if the 2-stroke oil has a higher specific gravity than the diesel (which I think is likely).
What I'm thinking of doing is syphoning out about 5l (or more if I can find a larger fuel container) from my freshly filled tank and mixing 225 ml of 2-stroke oil with that and then pouring the resulting mix back into my tank.
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