If he were to do that, I would feel more comfortable having the silicone on the side of the foam that faces water and dirt, not on the inside surface he can reach. I don't know if he could jam a piece of hose on the end of a caulking gun long enough to get most/all of the way back. Whole point of the foam is it would expand where it needs to go without having to get super crazy.
If it is rain running across the ground or off the roof that is pooling up next to the house before it soaks down and runs in, it can help a lot to add enough dirt next to the house to create a slope out for several feet (ideally, slope until it runs away somewhere else but a few feet is better than nothing). If you can dig a swale (shallow ditch) along the house and "daylight" it further away, that also works (great tractor project!). I am amazed at the number of people who complain about leaky basements have yards that slope down toward the house. Sometimes it is even "Oh, there use to be a ditch there but I filled it in to make the yard even..."
If you have gutters, extended downspouts and splash blocks help. 3 of my 4 downspouts have horizontal extensions at least 2 feet long. The 4th ends in a drain tile and goes out to a dry well.