How to replace siding around deck

The type of siding shown in your picture is most often used to serve as both the siding and sheathing all in one. A common term for this plywood material is T-111 plywood.

You would do well to check your house construction to see if there really is a second sheathing layer. If you find that the T-111 is nailed directly to the outside of the studs you may want to reconsider removing it. Because if you do you would have to come back at more expense to install sheathing as vinyl siding cannot be mounted directly to studs. The better strategy is to just install the new siding right over the T-111. If you do that you can then just use the pocket trim at the vinyl ends just butted up to the deck and caulked at the join.