I was originally thinking, something more basic, have a shaker feel to it. After looking at examples, It think my original plan may be been a bit basic.
Here are a couple examples of my first thoughts:

Or this window Example

Source: http://lovegrowswild.com/2015/09/farmhouse-window-trim/
Now I am now thinking of going with a more detail and definition. Hopefully giving a little more detail to the trim could go well with the reclaimed hardwood floors.
Table of Contents
Craftsman Moulding Ideas and Inspiration
Craftsman Door and Window Ideas
- https://burlapandtin.blogspot.com/2013/06/new-doorways-say-hello.html?m=1
- http://www.thriftydecorchick.com/2014/03/my-love-chunky-trim.html
- http://lovegrowswild.com/2015/09/farmhouse-window-trim/
Craftsman Baseboard Ideas
- http://www.thejoyofmoldings.com/wp-content/uploads/2012/04/baseboard-100_craftsman-style.jpg
- http://pilotproject.org/photo/craftsman-style-baseboard-trim-16.html
This is still the basic baseboard but maybe we give a little extra details to any of the cased openings.
https://gripelements.com/wp-content/uploads/2017/06/plain-baseboard.jpg
Moulding Resources
The Joy of Moldings This is a fantastic website with great ideas and resources.
http://www.thejoyofmoldings.com/craftsman-mission-style-moldings/
Craftsman Trim Install Guides
- https://www.remodelaholic.com/diy-easy-craftsman-window-trim/
- https://www.schoolofdecorating.com/2014/02/how-to-install-craftsman-style-window-trim/
- https://www.keystoinspiration.com/diy-modern-craftsman-window-trim/
- https://www.bloglovin.com/blogs/teal-lime-3896615/how-to-install-craftsman-style-window-trim-2418648975
This one is a little fancier wtih the angled parts at the top

Craftsman Moulding Systems
Windsor One: Also during my reseach I found Windsor One. It is a whole system of historically accurate mouldings. They have a Classical Craftsman Moulding Product Line with a lot of good ideas.
Home Depot: I do not have a link but I think Home Depot has a Craftsman Moulding System
Here is a pinterest board with lots of examples
https://www.pinterest.com/explore/craftsman-trim/?lp=true
Our Plan Starting from the Top down
Top of Wall — Cove Moulding got the idea from this page https://windsorone.com/back-of-the-board/streamline-builders-finishes-up-for-a-white-christmas/
Top of Windows & Doors — http://cf.lovegrowswild.com/wp-content/uploads/2015/09/Farmhouse-Window-Trim-18.jpg

Bottom Of Windows
Baseboards —
Thoughts?
Think it will come together nicely?