Can you post up some pictures?

That would help us visualize what you have going on and what might be an applicable solution.

Thanks.

Sorry it took so long for the photos. In the photo you can see where we covered part of the house with the cheap cedar shakes just to protect it a little from the elements. My husband put a thin piece of wood around the edges of the window and caulked that to also cover any gaps. We plan on covering the house with fanfold before siding to A. Avoid ripping down the existing siding and B. give the house a little extra insulation (our has was never insulated properly). With the addition of the fanfold the strip my husband placed around the window won't be wide enough and there will be a gap. How do we approach the windows? I see a product that is thick vinyl casing that looks great in pictures, but I don't know if that would be a solution. Or should my husband just build out wood trim? Or is there another solution out there that we're just not seeing because this isn't something we usually so?

Here is another photo to get an idea of just one of the sides of our house and why we are the ugly house on the street lol

Another close up (so I can only post one at a time)

I'm afraid my recommendation would be to call a pro. That looks like a real mess, and by the looks that siding could possibly contain asbestos.
Any of composite trim products available would install in the same way that wood trim would. They could certainly be used, but from what I see you have more work here than just slapping on some new trim boards.

Are you recommending a pro because you think it's asbestos? It does look like it is, but it isn't we've looked into it.