My partner and I have ample experience with wood shingle siding. I am finishing up a job right now but can be available for a walk through and provide you with an itemized estimate if you are interested. You can respond to me here or on my work email: J4architecture@gmail.com
Best of luck,
It's definitely worth joining the Boston Building Materials Co-Op, as they maintain a list of local contractors that they have experience with. All of the recommendations we have gotten from them over the years have been great! They are right over the border on Heath Street in Roxbury:
Good luck with your project!