How can I repair leaks in metal wrapped wood gutters?

Question

I've noticed a good bit of rain water leaking through what first appeared to be my gutters on my roof. When I got on the ladder and took a few pictures ( attached ), I noticed I've got wooden gutters that have been wrapped with thin metal sheets. The sheets look like they were originally nailed into the wood gutters and sealed around the top / side of the wood gutter. The sealing has started to come apart, and there are missing nails along the length of the metal wrapping.

So my first question is: how should I proceed to fix the leaking? Re-sealing the metal to the wooden gutter and re-nail the metal wrap into the wood gutter ( if so, what kind of sealant / nails )? Replacing the whole gutter system? Replacing the metal wrapping?

The wood actually looks to be in decent shape, but from what I've read, I'd have to paint the gutters every few years, and that's why the previous owners likely chose to cover them ( the whole house is now vinyl sided as opposed to the original wood ).

My 2nd question is: what's a good way to check for damaged external siding (my original concern when I saw there was leaking under the gutters)? Hardly any water is making it into the downspouts that are cut into the end of the original wooden gutter. Instead the water collects at the seam of the metal wrapping and drips down. I can't tell if any water is getting behind the gutters and causing any damage.

Answer 1

Hardness is a good way to check wood for damage without pulling it apart. Take a nail and press it into the wood where you know the siding is in good shape. Then, do the same where you suspect damage. If the wood is softer, then you can assume it has some amount of water damage. If you want a more direct, verifiable method your best bet is to yank a shingle or two off and check behind them. (From the pictures it looks like you have shake but its hard to tell.)

Also, as Steven commented...remove those "gutters" as soon as is humanly possible and replace them with actual gutters. Each year you wait things will get exponentially worse. If there is not currently water damage (which I doubt, sorry) there will be very soon.

Answer 2

While the consensus so far has been 'get rid of them', my first question was, how to work with them? I'm not looking to just pay money to get rid of something that could've lasted for over a hundred years just fine. My first question is still unanswered, how to repair the metal wrapping over the wood? Going further, how would one restore the wooden gutters?

I found this site which is a great read, and from their work you can tell which products may be used to restore or repair wooden gutters:

http://www.custom-carpentry.net/jobs/Newton-wood-gutter-restoration/

They recommend a few products to do sealing and / or repair work on wooden gutters:

Seal with Geocel's 50yr tripolymer sealant or coat an entire new gutter with Geocel's clear brushable liquid rubber

Installing and maintaining wood gutters seems to be going the way of wooden siding on these older homes (replace with vinyl and never do maintenance again!), but we are forgetting the lost appeal and art of using and maintaining real wood.