I also believe if the OP is a UK citizen then sending him iPlayer files would be more of a legally grey area.
I dunno, that seems pretty clear cut..
BBC Online Terms of Use 3.2.3 (d):
"you may not, and you may not assist anyone to, or attempt to[..], copy, reproduce, lend, hire,[..] broadcast, distribute,[..] transmit or otherwise use in any way BBC Online Services and/or BBC Content in whole or in part"
this ^^^^^
i live in the UK and sending him iPlayer files is just as illegal as selling weed on the street
The reason I would have claimed legally grey is that if he had a right to watch them anyway, but simply could not through a legal manor due to the IP restrictions.
If the files were downloaded directly to a USB the only part of that which could be mentioned would be distribute, and since I my offer was not to make profit (When you consider all my costs (postage, media, bandwidth etc..) I doubt very much a case would be made against me. Common sense and most courts would throw the case out.
However I was slightly wrong. The part of the Terms I would have mentioned is this
3.2.1 If you are outside the UK
You may not access, view and/or listen to certain parts of BBC Content (such as video or live television services) using BBC Online Services if you are outside the UK
Which does change things a little.