Charming period house, the three center windows are cute but need to be one type, and the sliders on both sides seem random... Any photos of what the house looked like early on?

Regarding stucco, it IS very hard to make repairs completely disappear. I don't mind seeing a well done patch, I prefer that versus re stuccoing an entire home so it looks perfect. I also don't use synthetic products, stick to the cement based stucco the house always had and you will be fine.

Finding someone is the hard part. We are in a building boom so tradesmen are focused on the big jobs not repairs. You may have better luck hiring a GC who can wrangle the stucco guy (he can then coordinate the window install as well) Just get one used to old houses versus new.

A million up-votes for Hallett's advice.

I remember this house. How are things evolving? https://www.houzz.com/discussions/4903654/architectural-style-of-sinfully-ugly-stucco-house-and-how-to-fix

Apple Pie my friend I won’t tell you that it has improved. Amidst the wistfulness of leaving our 1850s house for this new construction, I’ve also realize that our stucco situation was constructed for dwarves which is especially unfortunate given that we are giants. I’m 6’, my husband is 6’3 and I now have four sons who I just assume will be taller than both of us. Meanwhile, both the third floor and the basement are useless to us with ceiling heights at 6’. Brutal. We would move, but the neighborhood is a dream come true. Also, we love having a pool which provides a healthy outlet for so much great family time, and makes us a social epicenter which we love because we love to entertain. Even if we could find another house in this neighborhood, ours is easily the largest lot and none of the others have pools. So we are stuck here- for better or worse. We cannot add up because the slate roof makes that cost prohibitive. I have explored digging down but it does not seem to be an evolved practice here in the Midwest.

Did I mention that it has really only three poorly situated bedrooms and no rec room? Honestly I would forget about the bedroom situation if I could have a giant semi finished basement where my almost basketball team can run themselves ragged in circles. Four boys age 7 and under. What we really need is a human sized hamster wheel!

Google "excavation companies specializing in existing basements".