VERY LONG REPLY, SORRY ABOUT THAT.
We have done 3 similar renovations, though neither involved changes to the houses' footprints.
1. Our Westport house had an attached screen porch that was truly just screens, no winterizing functions. Snow would blow in and chipmunks were tunneling up through the stone floor where the pointing had eroded. We loved the end result: made it three-season with a heated floor, included removable glass panels for winter, etc.
2. Above that screened porch was a deck. During the porch reno, we learned that the entire deck flooring above was completely rotted so we had to replace that too. We used Trex for the flooring and my one caveat is it was treacherously slippery when wet unless scrubbed regularly. That was 2016 and I'm sure things have improved.
3. Fast forward to right now, in our New Canaan house. Similar thing: a downstairs porch roof was leaking because - of course - the small deck/porch off our bedroom was completely rotted. Just got completely rebuilt including the railings and is waiting on repainting. Again, artificial wood flooring but I'm hoping the slippery factor has improved in 8 years.
A few photos below. Waiting on Mr. A to send me one of the current project.
First photo: the "after" on the Wesport screened porch. No shots of the deck, somehow, but if you look at photo #2, you can see that house from the front, as an example of an architect's seamless blending of old and new.
The entire left portion of the house was added in 2012, not by us. The smaller right side was the original 1835 house. It's the side with the cupola and the date plaque near the "old front door". Everything to the right of that was a modern addition.
Photo 3 is the Westport porch in progress.
I would recommend finding someone who understands what you're after to help you, if budget permits. In fact, after doing MULTIPLE renos, I would say this is the most important expense you'll incur, even if it means delaying the project.
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