It sounds like morwil did not hire the installer, the windows were put in by whoever s/he bought the house from. Did the previous owner do it himself, or hire a contractor? Is there any way to find out whether there is a warranty on the windows or the installation? Hurricane winds can drive rain into places it would not normally go, but if there is no visible caulk it may indeed be a faulty installation. Insurance coverage is going to be a question for your agent. The cost of having this fixed is going to depend on what kind of siding is on the outside of the house. Windows are put in from the outside, so the outside wall will probably have to come off around the windows. It's going to be a different job if it's vinyl, wood, brick, etc. And of course how many windows there are.

Does water actually pond against the window frame or siding when it rains? If so, you are probably right, and I would say you should lower the grade somehow (rather than depending entirely on french drains - which will invariably clog at some point). My first suspicion with moisture problems around windows, however, is some kind of rainwater leakage through the wall somewhere around the window. Because of gravity, it will invariably first appear at the baseboard or wall under the window. Check closely (or post pictures of) the flashing around the window on the outside for possible rainwater entry points.

Hi, That picture in my initial post is from the Erie Art Museum in Erie, PA where the window is currently displayed and I cannot take closeups of it since I am at home in Maryland. But here is a photograph that demonstrates the non-invasive attachment of a camera. My basic idea is to replace the passive sash stops that all these vinyl windows have at the top of the jamb liner track with 'active' clips that can be actually quite useful in decorating the window without damaging it, its frame or the walls around it. Right now I am printing these clips in ABS at home on my 3d printer and they are very reliable and quite good looking. Normally they should be injection molded or extruded from some thermoplastics if I ever get to make a lot of them.

Since no one has responded, I'll tell you what I think as a homeowner (not a pro of any kind), and my response will help bump up your thread, too. Water needs to flow downhill, and water shouldn't be sitting damp near your foundation. (nor around your fence, imo). I'm an amateur here, but I think you need in-ground drains that are sloped towards wherever your water needs to drain toward. In my tract neighborhood (SoCal), in ground drains throughout the backyard, drain into underground pvc pipes, that go out through the front yard, through the curb, into the street gutters. I don't know where you live or how ground water is handled where you are. With those issues I see in your photos, I'd call my gardener, who could install drainage pipes and drains in the ground in a day or two, maybe with one guy to help him. I would also ask him to slope the ground away from the house for good measure. My gardener routinely does that kind of work. On our house, every gutter downspout lets water out into a ground drain. I dont know why you don't have in-ground drains, but again, I'm not an expert. There are people who do only gutters, and you can check your Nextdoor website/app to find someone to adjust the downspouts, once you have proper drains.