My advice is to remove enough material so that you can assess what the cornice construction looks like in section. Then you can be sure that the holes you drill will actually vent the roof. Otherwise it may be wasted effort. Don't drill up thru the gutter! Casey

You don't want to replace them with modern gutters, as that would spoil the look of the house, and lead to clogging with leaves. My box gutters were lined with rubber about twenty years ago, so I guess I should check the lining. :) I'd say, remove the rubber, clean the metal, and replace the rubber--I wonder if that ice dam stuff would work, or if it degrades from sunlight? Perhaps when you replace it, have it overlap the top outer edge enough to be tacked down as well as glued?

kjb - those of us with old roofs usually have old gutters to go along. We have box gutters and more than likely the same problems. If you have not yet gotten a quote for repair of your box gutters be sure to be sitting down when it comes in. Without knowing the size of your house I cannot guess how much your gutters will cost to repair, but to reline gutters can cost tens of thousands of dollars. We got the quotes and realized we just could not afford that. Ripping off the gutters and putting in something else was not even an option in my mind. First, it would not be that much cheaper, and second, it would change the look of the house. We had a guy clean our gutters, patch really bad spots with epoxy and fiberglass, then paint the inside with pickup truck bed liner material (Herculiner in our case). He told us it has worked well for him in sealing leaks. In our case, the leaks continued. He was going to come back and put on a second coat, but while I was waiting I tried doing one gutter myself with a liquid EPDM rubber. This stuff gets painted on and sets up like a flexible rubber liner. It is only a month or so old so I cannot know how it will hold up, but so far it is working well. It is supposed to last for years, so I hope this has bought some time. You can read a thread about box gutters over at the Old House forum at http://ths.gardenweb.com/forums/load/oldhouse/msg110817128649.html?12

This looks like someone's brilliant, but bad idea. Someone is possibly trying to kill two birds with one stone by using downspout water to water the flower box, or they're trying to drain the flower box through the downspout tail. In doing so they've put a box right up against a wood fence so the fence won't dry out quickly and will rot away sooner. Why is the box necessary? There is dirt already at the edge of the walk. Plant directly in it. The gutter tail is buried shallowly. Please show where water empties out of it. If it has to come back up to the surface in order to empty, that's pretty much an eventual guaranteed clog. I would extend the downspout to a normal length (to about 12" above grade.) Attach a gutter tail, above grade, that extends about 3' or 4' -- beyond the stoop. At the end, possibly direct the water onto the walk with angle attached to the tail, whereas the walk is acting as a splash block. If not doing this way, you'd need a splash block at the end of the tail. (If this creates other problems, share information about them. We can only see a limited amount of information from these pictures.) Creating proper drainage is of the highest priority. Pretty flowers is secondary and comes after drainage is corrected.