It would appear from the photos that the second hose clip does not have enough room to press the hose onto the metal of the gland. This has probably split the hose around the end of the gland and has caused the leak. If this is so, no amount of tightening the gland nut will stop the water from coming in. The only solution is to replace the hose as soon as you can.
>The packing will be pregreased and is tightened by rotating the packing nut
The leaking problem could be that the packing has worn out and needs to be replaced.
To remove the old packing use a screw. Check the size of the packing and cut to the shaft diameter with 45 degree angled edges that 'lock' together. Push the packing in carefully with a screwdriver, making sure that the cut in each piece of packing is 180 degrees to the previous one. When the hole round the shaft seems full tighten the packing nut(s) until the nut(s) are tight then loosen them and check if there is space for more packing, there usually is.
The whole assembly looks dodgy to me. I can't make out the usual gland nut/lock nut arrangement. Vyv Cox's website contains lots of pictures of different types and information you could look it up on that. My advice is to replace the whole sheebang the last thing you want is a major unstoopable leak. I've just sold a complete unused assembly for £50 so they are obtainable cheaply.
Your mate could strip and rebuild the existing unit - the leak is either worn packing or split hose. Or take the opportunity to replace it with one of the more modern drip free seals such as a Volvo, Tides Marine or PSS. You will find descriptions of them on Vyv's website referred to already.
If out, it is ok to take out and replace the old packing and gaiter.
If still in DON'T or you will see what a major leak really looks like
but what you can do as a temporary measure is to undo the packing tightening nut, take a length of cotton string covered in waterproof grease and wrap it four or five times round the prop shaft in the opposite direction to the way of the forward shaft rotation, then tighten the packing tightening nut on to it.
If the gaiter is split, bind it with self amalgamating tape and maybe two or three tie wraps.
Thanks for replies so far, his boat is in the water and we understand about split hoses and packing but can not see which parts to adjust, the usual nuts are not obvious. Must try and clean up with wire brush to see if there are threads or a joint. Sod of a thing to get at and will proberbly end up taking out of the water, he is on a tight budget so these things are all relative. Vyv Cox's site is very good but still not seen same gland.
Have managed to clean it up a little and can now see the join between adjusting flange and locking ring. Only three castlelations ( spelling )on the flange for the locking tab seems unusual. Will give it a go tomorrow.
It's somewhat different from any I have seen so far, so I will add it to the website with your permission. If you are stripping it perhaps you could take some more photos?