Thank you pixie_lou and hollysprings for the fast replies! We've been struggling on how these pieces of the remodeling puzzle fit together. Earlier phases like electrical service and roof insulation were much easier to compartmentalize. If we do the window and insulation / siding work at the same time (or within the same year), can we start on things like the ISO install several weeks or more in advance of the window contractors arriving? We'll be doing the insulation work ourselves and it will take longer because we'll be doing it on evenings and weekends (weather and work schedules permitting). We've done a lot of the work in our houses ourselves and it's always been the timing between what we do and what contractors do that we struggle with the most. Because we both work full-time, and with DIY needing to rely on a lot of research both before and during work, our work pace is a LOT slower than the professionals.

Check that the drip edge (if you have one) or that the terminating edge of the shingle overhangs the gutter. Check that the gutter downspouts drain, no clogs in the downspouts. Check that the gutter is properly pitched and not sagging in the middle, resulting in water accumulating in and then water is overflowing out of the gutter. Is the roof area draining into the gutter overly large? Gutters do have volume ratings. If water was getting behind the gutter, it really should just drip between the back of the gutter and the facia. As to it getting from there to behind the siding...it could be anyone's guess based on soffit an siding details. If you had significant amounts of water getting behind your siding, there's a pretty good chance that if it was over long-term and not just recent, you'd have paint adhesion issues with the siding, as well as issues on the interior wall, or water wetting the basement wall on the interior side of the foundation, not just below grade, but above grade. I'd venture that it might be water getting out of the gutter and running down the face of the facia, and then down the surface of the siding, but not behind the siding. That's less likely if you have a deep soffit. But you never know. Best of luck!

First remove the shutters , you need a walkway from the street to the front door . I like gray/ green with brick and this is a good example of how good it looks. If you can do like this and paint the trim the same . You need a MCM door could be a color other han the siding or the same. Then it’s landscaping that will bring this house to life . I don’t know how far down the MCM rabbit hole you want to go but this is a favorite of mine

If you replace it, you could always do a Hardie product that looks like cedar shakes, and they come in lots of colors. https://www.jameshardie.com/products/hardieshingle-siding?loc=refresh