Find another contractor! The footing needs to be drained. Otherwise water can still seep in. In very wet areas and some soil types like clay I have found that using both an interior footing drain and an exterior are needed. Don't compromise on this. You will forever regret it.
Just make sure no pieces of gravel fall beside the box or worse under it. Then it won't roll. Good idea for a pickup truck. I just use a trailer.
Where there is caulking it will fail. Just give it time. The best way is to use ice and water shield around the window. Ultimately it comes down to the installation more than the method. As for fiberglass it only works as an insulation if it remains uncompressed. As soon as it is compressed it is no longer effective with the designed R value. It also only works if there are no drafts through it. This is a hard thing to achieve with fiberglass. Traditionally its purpose has been to stop drafts around windows by "stuffing it in". An old sock is just as effective in this case. The dilemma is what happens if it gets wet or moist. Heaven help you then. The chances of it drying are slim. Spray foam will provide an R value as well as not absorb moisture. Plus it stops air infiltration. Why would you use anything else?
Absolutely love the wood. To think most people paint it. Fantastic job!
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