Billy's gutters

I gave Billy a really good wash today. A proper deep clean, with sprayey bleach and a toothbrush in all his difficult to reach areas. I think it was actually the first time I've ever cleaned his gutters, since I got him - there was a lot of black crap in there, and it seems it was covering up a world of sins.

I remember when I first got him, and he was freshly painted, there were some quite bad leaks in the gutters, which I fixed with some squirty silicon to keep the interior dry. Well... I think the holes I covered up have got bigger.

Wondering now how to fix this... will it require getting someone to weld on some new sections of guttering, or maybe a bit of filler at this stage is ok?? I'm going to ask the forum.