Here is where we are with exterior:
Disclaimer: While both photos were taken by phone (I really DO need to start putting that DSLR to use), second happened in late spring and sunshine which definitely helps with overall look and improvements that were made. Talking about improvements, just what have we done:
2. On original fascia boards were painted dark green and were quite wet all the time preventing us from painting them out as I wanted to match them with front door colour. Our roofer provided a good solution by covering the boards with sheet metal. There were a few options in terms of colour and selected the one that I felt would work the best with shingles and rest of colour scheme.
3. For roof shingle replacement we decided on contractor first and shingle second as the contractor worked with certain brand. While we were reviewing contractors I've had my eye on Certainteed shingles, particularly Highland Slate shingles to give the house some additional interest and adding some whimsical quality to house since we were stuck with shape of the roof. I really wanted CertainTeed's Carriage House shingle, but that was out of our budget.
As the contractor worked with IKO shingles we decided on Cambridge Architectural Shingles - Harvard Slate colour.
4. Our top windows do not match our bottom ones in neither style nor colour but are thankfully all three the same. We decided to blend them with the shingles instead of making them stand out and we covered them with same metal sheet as we did fascia boards. We might do some work on them - either shutters or window boxes or both depending on what we find.
5. We looked at couple of exterior lights but settled on these ones as they best emulated door trim. They are from Home Depot but I cannot seem to find them on their website anymore to provide more info.
6. Trim we decided on ourselves by buying different decorative elements from Home Depot. The very top was not finished exactly how I wanted it as the contractor made the cuts on his own - but I've learned to live with it.
7. House numbers are the same as the one in the original picture just spray painted black. While I wanted to replace them originally I could not find anything I liked that would work with rest of the exterior so we thought it was best to save a penny or two and just reuse. Since then I found nice and affordable house numbers at CB2 at $10/number that I think would have worked well as well.
... to be continued...