Ok there has been some great lens selections here however.... (this is just my personal opinion and may be slammed by many...) I would buy the 430ex with an ettl extension wire (for off camera flash), get the 50mm 1.8 for your low light shots, and the next bit is where I get controversial get the 55-250 for the long range shots you mentioned in the original post. The 55-250 is a great little zoom for the price with nice IQ. That comes to $601 plus $20 for the wire, ok lets call it $650 to be pessimistic. Ok the really strange bit... I would KEEP the 18-55 and spend the money on a "foundation in photography" course for your colleague. At this stage it would probably be of more benefit than any "better" lens..... I have seen some great photos come out of the 18-55 this is why i would keep it. then if you have money left maybe a photo editing software.
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