Help With My New Windows

[Mrlamo]

Ok,

I have (I'm guessing) vintage 1970 Pella Casement windows everywhere in my house. Several windows that have leaked so bad from not closing properly (caulked shut now). The leaking has caused the drywall beneath the window to crack, hence I'm guessing there is some rough sill rotting going on down there, water damage at least.

The Plan

Remove the windows down to the rough opening, remove the capped brick molding, and leave the j-channel(I have vinyl siding). Replace whatever wood needs replaing, maybe drywall too, ugh!! Then replace the windows with Simonton 5500 with the nailing flange. Then put up new solid vinyl brick molding and caulk where I need to caulk.

I have done windows in the past and have several years of general construction experience.

Can anyone tell me what I am missing, or why this would or wouldn't work.

Oh yeah and I checked, the j-channel is not nailed into the brick molding capping, so it won't be that hard to remove.

I've also heard from this forum that, I should put a thick bead of caulk on the back of the window nailing flange, before I put it up there...I assume they mean like you do at the bottom of a pre-hung exterior door.

Any help would be great.

Also I sent out a list to a few people for the windows, 8 DH, 2 sliders, plus a bay. My best quote so far is about $4000, does that sound about right for the Chicago Area.

I will be installing the windows myself.