This is how I installed my board and bat siding.
The wall framing is sheathed in 1/2" ply so that even with the minor gap between boards, and under the batt, it is not open to creatures entering the bldg. I prefer continuous boards and batts I think it is a better look and less chance of water penetration.
As to weatherization of this kind of siding; I used two layers of building wrap and vycor at the wall corners and openings. Not saying it won't leak but this is a fairly weather tight detail if done correctly.