vinl siding question

My house has masonite siding that is on furring strips over wood siding. I am wanting to put vinyl on the house. Do I need to remove the masonite to have a better nailing surface?

 

Some go over it with 4x8 sheets of foam, others use fanfold insulation, which comes in 200 sq ft bundles (4' x 50'). The insulation helps give a flat surface to nail to. The really cheesy installers just put housewrap over the siding, and then try to be careful not to drive the nails too deep. Many contractors go right over the existing siding, but its usually because they just want to put up the siding, get paid, and go to the next job. Removing the old siding just takes them extra time and would make their bid cost more than everyone else's, and they wouldn't get the bid, because the bottom line in who gets the job is usually who can do it the cheapest.

Going over your existing siding with even MORE siding and insulation will add thickness to the wall, making windows and doors appear sunken in. IMO it is always best to remove existing siding before installing new siding. Kind of like how you would remove existing carpet before installing the new carpet.

But you would want to establish that you have some sort of sheathing behind the masonite before you go ripping into it. And once it is removed, you would want to apply a weather resistive barrier (WRB) before installing any siding.