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You are right to be concerned about what happens when you add insulation to older structures. I'll defer to other folks that have experience with similar assemblies, but the main risk is if the stability of your current sheathing is dependent upon its being able to keep dry by means of a continual supply of heat through the presently uninsulated cavities, you could be in trouble.
You should scrutinize areas where water might have a tendency to get through your siding layers. Typically these are at roof/wall intersections and windows. If no water ever gets to your sheathing, it could be a moot point. But it's hard to know that definitively in older buildings...