So, you guys fancy helping me spend some money?
Ahhh my favourite subject
Body: 60D, I'd like to dabble with video and feel I might outgrow an XXXD quickly. This feels like a logical choice for me. Is it worth getting the kit lens with one or body only?
It all depends on your budget, but if you are looking at the second hand market the 50D is worth a shout and the 40D is still a damn good camera! Which leaves more opportunity to decent glass.
Prime for portraits and walkabout: 50mm 1.4? Any particular brand?
Whilst the 1.4 is far nicer than the 1.8, for what you will be doing I think the 1.8 will be fine
saves you some pennys.Lens with a bit of reach? Really not sure what to look for here.
Sigme 70-300 is a good shout and starting point
Tripod: Redsnapper with ball head?
Only ever bought manfrotto's so can't comment, although Redschnappahs are supposed to be very good!
Off camera flash? No idea here.
Filters and diffussers for items above? No idea here either.
Wouldn't worry about that for now, however I would buy a 430ex II flash
Battery grip? Best to stay with the official Canon?
Grips for the XXD cameras are cheap so may as well

