I have done both stamped concrete and paver jobs. I don't have a negative opinion of stamped concrete as do some of other pros in the threads running concurrently about this subject. However, concrete is like cooking; there are many variables. Stamped concrete adds more variables. Therefore, it takes a very experienced subcontractor if one wants to make sure of the outcome. And not absolutely everything can be controlled 100%. If you can find a really good sub -- whose prior work you've inspected -- then you can probably get a result you like. Pavers are easier, and more easily corrected if there are errors to fix.

Kristen- I see a Screened Porch on the deck above to provide a dry area below. Seems like a perfect fit for your nice home...and you did say that this could be a multi-phase project :) I would add lattice work around the posts underneath and gravel as a base for storage accessed by a lattice framed door. Electronics could go against house midway back. Can't tell from the photos how much headroom you will having after excavation down to the footers. You may indeed have enough height for a use an enclosed room. Doug

What damages concrete in winter is melting chemicals, especially ordinary salt. What happens is this: During the day during maximum temperature, the chemical melts snow and ice and the brine penetrates porosities in the concrete, then later at evening and night if the temperature falls below the freezing point of the brine, it freezes and pops off chips of concrete. Talk to your concrete contractor about this. He can select a mix that is more resistant to freeze spalling, usually a greater amount of cement to sand and gravel (and greater cost). He may recommend a sealant. Do not start the project too late in the year. There is a wait time before applying sealant. Its best to have the recommended curing time before applying a sealer and before freezing weather sets in. Many times, the fine, smooth finish layer is more susceptible to damage than the underlying base concrete, It has been my experience that sealers do help but are not 100% effective. Expect damage after 3 winters of salting. One of the very best things you can do is to shield the stoop immediately in front of the door from snow and drippings from the main house. I recommend a portico (roof projection) over the entryway. Its roof should be shaped to direct house roof drippings away from the stoop and the walk. After a snow, clean the stoop before trampling the snow and welding it to the concrete. Before you begin your project, educate yourself about how to make concrete resistant to cyclic freezing-thawing. This is big problem in northern climes and reduces as one travels south.

I have (had) painted my stamped concrete twice now, two different colors since the original, and it comes out great and lasts a few years. It just needs to be a specific kind of outdoor paint.