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
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:
Hi Terrell- I own a condo in JP and have done various renovation projects. I can vouch for the work of Jason Robichaud (also a JP resident) who responded down below. Excellent communication, very fair pricing. Regards, Jeremy