Re-roofed: Need advice on dormer re-siding

I recently tore off a 35-year-old 3-layer shingle hip roof in MA. I put down new drip edges, ice/water shield along roof edges, valleys and hips, 30-lb tar paper, new flashings along dormer sidewalls and 30-year architectural shingles.
I had to take off all the dormer siding (vinyl siding, flimsy 1/4" styrofoam insulation and old shingles) to properly remove decayed flashing and properly install new flashing. Now I need to re-side the dormers.
They are sided with 1x's of various widths...all in ok shape. I would like to put some foamboard insulation down prior to putting on new siding. What would be the proper materials...and the proper installation sequence? Tarpaper/Tyvek...Foamboard...Siding?
Second Question: If I install foamboard, how do I install it around the storm windows? Do I "box" in the storms with the combined foamboard and new siding? How do I avoid having exposed foamboard on the interior dimensions of the window "box?" Not sure if I worded this quite right.
Last Question: Rake boards along dormer side following roofline...Yes or No? I see a lot of dormer siding in water-decayed shape around here due to bad spacing between siding application and roofline. Should I just allow proper spacing for water runoff and no rake board? Or install rakeboard with proper runoff spacing?
Thanks very much!
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