Never thought I'd ask one of these again  :) 

So, long story shortish. 
A friend of mine lost his job (factory close) awhile back and is running low on cash.  We've taken care of his bigger money problems and now he's  left with one bike as his only mode of transport....  So I was helping him fix it up and the last thing on the list is it needs (badly) an oil change.

I have a few oil filters (from my 09) that will work and 9 Liters of Castrol edge Sport 25W-50 sitting in my shed from when I had a Sportster.  So I was wondering if we could safely use it for an oil change in an 08 (I think?) Harley Davidson Streetbob?

Absolutely - use it . (probably not in the primary though)
Maybe a touch thick, but way better than leaving the old crap in there.
It's probably even a good choice for the warmer climates.

Thats a good summer oil!  Go for it.

Well that should make his day :)   Turns out I've had all the stuff he's missing (or broken) in my shed - including a headlight, slipons and mid controls I forgot I had.

I also found a 4litre of Castrol Active4T 4 Stroke Motorcycle oil.  15W -50. No idea where it came from.
Two 1Ltr bottles of Castrol Transmax Type F
1 1ltr bottle of Nulon 75W-90 semi syn manual gearbox and transaxle oil

I get the feeling that at least the bottom one is a double I bought for my 09 Streetbob when I first got it?

you could even run the 15/50 in the Primary if he has run oil to date + thats a perfect oil for summer/winter.

these big twins will run on anything besides olive oil.

Done some remembering and I think (on two different bikes) I used:

transmission (Nulon 80w/140)  (.95 litres?)
primmary Castrol trans fluid type F
engine  (Castrol Edge 25w 50)

I'm thinking it should be the same for an 08 model and from what I read oil lasts as long as no moisture gets in.

Bonkerz, your mate is lucky to have a bloke who can help. Good on you Mr.B.