So I'm putting in new construction windows and have to remove portions of the vinyl siding for the nailing flange, seems easy enough... Well, whoever put this siding on my house never removed the original wood siding. Instead, they just put some foam over it and slapped the new stuff right over top of it. Needless to say, this presents a bit of an issue with sealing around the area where I have to cut for the nailing flange, as it will now have wood exposed if water were to get back behind the siding around the windows. This means I either need to find a way to seal around this area, or I have to remove all my siding and redo the whole thing (I will probably do this later, but am not prepared to do so now). Luckily, the window I did yesterday is under an overhang, so water isn't an issue, but with all the other windows water will be a problem. I was thinking of possibly using a spray type sealant for now, but wanted to know if anyone had a better idea. [ATTACH]72642[/ATTACH] [ATTACH]72646[/ATTACH] [ATTACH]72645[/ATTACH]

So a small section of siding trim (which is very close to the window) has rotted. I have chiseled and sawed away the rotted wood. Photos of the rot after some sawing and chiseling: [url]http://imgur.com/a/bR5de[/url] So now I'm looking to fix this before winter hits. I'm located in Eastern Ontario, so lots of snow, and the wall is north facing. Here is my plan, please let me know if I'm missing anything crucial: 1. Insert a piece of wood, 4 1/8th of inch in height and cut to size, into the vertical trim gap. Caulking will be applied to the back, top, and bottom of the wood piece. Nailed it in. (making sure to nail to the wood stud, not the metal drip edge). 2. For the small area to the bottom left, either cut out a rectangle section, and insert another piece, or fill in the gap with exterior wood filler. Still deciding. 3. Caulk and repaint. Now, I just have a few questions: A. looking at 4th and and 5th picture, it looks like the bracket that is used to hold the under-window sidings has a gap in it due to the way it is nailed. There is also a gap that go directly into the walls. I suspect this might be one of the areas where moisture is coming in. When the wind is blowing in the right direction, the water falls into the bracket, and then flow towards the trim/sil, causing the rot. The holes are slightly bigger than my index finger. What would be the best way to seal the hole so water can't get in anymore. Can I just fill the section with huge amount of caulking before nailing in the piece of wood? What about window insulation foam? B. Would it be worth while to put in some adhesive flashing tapes or tar paper at all the places where I can? The trim is close to a window, but they are not quite window trims. I noticed that there is some old left over tar-paper that has already disintegrated. C. What caulking would everyone recommend? I have Dap Alex plus silicon. The can says interior and exterior, as well as water proof. Just wondering if anyone would recommend any better alternatives? I live in Canada, so selection might be limited by that. Thanks.