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Vinyl siding, I'm guessing is what you want to use. Has a starter that you want to use as much as possible. Any time you can't use a starter like when you have to cut the bottom peice then you are going to use "j" trim. So the height for starting is key. Siding comes in different configurations like 3x3" or 2x5" if you can find one that works so you get to use a starter on the side of the house and the front, that would be best. The corner peice is called corner peice, inside or outside.
Unless you are going with verdical then all of that wouldn't matter and you would use the small "j" trim for starter.
There are tricks to use wood for corners and window trim that almost completely hides the fact that it is vinyl and makes things like the corner beside the deck easier to deal with.
I would have no problem running a skill saw up the side of the house to remove the corner and work on the front, just wrap the house wrap long and tape it to the old siding to keep it waterproof until you get to that.
The structure and make up of the deck will need a close inspection first.
In my ealier instructions I missed roof venting. Correct me if I am wrong, no venting in the soffet of the house (roof hang over on sides of house.)
Is there venting into ceiling of the deck area? Is there vents on the roof of the deck or the house?
 
Soffet does not appear to be vented. Not sure about deck area question; its open entirely underneath, I can get pictures later (not at home now).

But yes, looking at vinyl siding. So remove front siding, inspect/etc, wrap and cut endges on the sides to open up the corners, overlap the wrap onto the current siding, and then tape it down while doing the install. Does that sound about right? Doesnt seem too bad (hahahah I know it's not a quick / simple job)
 
We always ventilate all roof decks, porches, garages, living space, unless there's been spray foam applied. Shingle MFG's require a vented roof deck to warranty their product. If there's no soffit (intake) vent, you can add a starter vent under the first course of shingles. It will require removing the first course, cutting the roof deck and filling back in the shingles IF there is a soffit board underneath and not exposed rafter tails.
 
If you put up vinyl soffit, PLEASE put all vented soffit, not every 3rd board. It's the only way to get adaquate intake vent area. It's better to have more intake than exhaust vent.
 
The more things change the more they get strange. They are building houses so close together that they have decided that you can't have open venting on the side of the house. We had to put in plywood like this house has and wrap the plywood for three feet on front and back. With a hip roof I guess the air will be drawn to where it is need but I have no idea what the plan is for gable style roofs. I suspect we will be seeing alot more houses with gables on the side of the house.
 
And last night was a late evening. I'm still getting myself into gear this morning, but I'm working from home and will be able to check on things, get pictures and all that today.

Roof venting: What should I be looking to see if that is or is not the case? Should I be looking for evidence of a fan in the attic, or is this something different?
edit: after some googling, I found this image:
MqdMNeX.jpg


If that's the case, I believe I have a whirlybird vent. I'll confirm today; but I know I've seen something that looks nearly the same up there.


Soffet: Not vented far as I can tell.

Porch situation: I'll get pictures later. It's fully exposed rafters underneath and I do not believe this is vented (but I'll explore more).


Also, good morning!
 
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You said you replaced the gutters, that just makes me think there might be a problem with venting and ice dams. The porch will need a vent to let the heat out in the summer and help the roof last longer. Later.
 
The previous gutters just looked like a bad home-depot job done by someone who winged it and didnt know what they were doing, I didnt see evidence it was caused by anything lingering but at the same time I dont know what I'd be looking for. Venting on the roof does indeed look like a whirlybird vent in the picture.

Working on posting images of all the fun stuff now.
 
Back with pictures.
ALL PICTURES CLICKABLE FOR BIGGER

Soffet: Not vented visibly. Upon closer inspection it is metal of somesort, and wrapped around over the fascia, and under the gutters. Holy crap. 1) It's really ugly, and 2) I think this is a bad idea based on every other soffet I've seen, no?

Porch underneath:



Then I have two windows as examples of what I'm dealing with. Any insight would be awesome; I'm open to restoring these at this point (and dealing with siding down the line sometime), just want to be smart about it.

Upstairs window
These have had drop in replacements done, but obviously framing is original.

The current state of the trim is kinda grim.
 
Part two due to picture limit:

Downstairs window
This is the window on the porch. It's had a storm window retrofitted over top, looks like it was just screwed in over the current trim :(




Inside of porch window, just for an idea of the frame. It barely opens and has what is obviously many layers of paint and years of ignoring it on it.
 
You will be able to deal with the doffet when you do the siding. There will be more things to address in the attic dealing with insulation as there should be space above the insulation so air can move over the outside wall to dissapate the heat that always appears there in the winter.
 
Chances are what you are seeing on the roof is a vent stack from your waste water system. They kind of look like what the photo you posted of the whirlybird. Not too often do I see a relatively new roof done with that type of venting. Most common is ridge vent I would think and then gable vents. You don’t have gables so it rules that out. Try and take a photo zoomed in, of the part of the roof that’s cut off in the real estate photo. Right at the peak and where the porch roof joins the house. Also a photo looking up at the soffit or overhang that’s clad in aluminum. The holes in that material are real small that let air in you might not be seeing them. The roof looks well done and in good shape and I can’t see a roofer doing that work without doing venting.
 
Porch roof, from the top and the bottom, no evidence of vents:


Soffet, showing no evident venting:
 
If the old wood trim is there you might be able to deal with windows first, you won't know for sure until you remove some trim and see what you have.
 
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