The build up (and required door ad molding trimming) is often the biggest problem. It often takes more time and effort to instal new flooring in older structures. The factory nailing schedule may be inadequate if the surface is not 'factory flat.' It is not that it cannot be done, just is more work. large humps will of course remain, and out of flat can also result in a greater chance of squeaks developing (especially if you adhere to a factory minimum nailing schedule).

Thank you, everyone! To answer the questions by skydawggy, the windows are vinyl. I haven't had the wood wrapped (yet)--have thought about it, just hesitating because of expense and so many other home improvement projects. And the wood is in decent shape yet. As for caulk: owner of company assured me that they do not use unpaintable caulk. One of the company's employees confirmed that this is the caulk that was used for the exterior: OSI VP-275. It says on the label that it is "not paintable" and "paint surface before applying." Seems pretty clear to me. To answer fusion866: thank you for the info. I know that many painters do routinely remove old caulk anyhow before they paint, since caulks do wear, crack, and so forth, and so they wouldn't want to paint over anything like that. I will not do anything to that caulk until a painter works on the trim (and that isn't in my plans in the near future--current paint job is ok)--in addition to risk of wood rot, I do want to keep water out from between window and wood,which is the point of caulking. I am just mad at the window company--they lied about quite a few things (how installation would be done was a biggie although of course that is a one-day nightmare that is now over). Maybe many window companies are bad -- a local resource that provides information about all kinds of home improvement and other companies noted in an article that most people are miserable with their window installers. Anyhow, thank you all for "listening" and for your responses.

It is best to prime all six sides.

There is probably a better forum, but I will comment on the idea of an arch over the middle window. I don't see how an arch fits with it. It would look contrived and out of place for there to be an arch when there is nothing that corresponds or fits with it. Nor does it look like a house that has any kind of arch theme going on. Stucco trim that fits with the existing features will look better.