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It's a free standing garage building... 14' x 20' OA with framed 2x4 walls 8' over a 2' block foundation with a concrete floor; about 30 years old and mostly solid but needs some TLC. Presently there is some thin lauan plywood stapled to the ceiling joists (or truss bottoms I assume).
It doesn't get much shade until almost sundown but it's still not too terribly hot inside except on the hottest days but I don't think there is any insulation in that "attic" space. I haven't been here when it was cold.
I'm not planning to heat or air condition the space or work in it beyond puttering on motorcycles and stuff like that but I am thinking about adding some ventilation beyond the two small windows and the roll-up door... and maybe some insulation too.
A heavier part of the TLC work is to re-roof the building and I'd ordinarily put a ridge vent in but with the "attic" space above that lauan sheetng all sealed up... I'm wondering if that's the right approach.
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For the most part- the insulation is a waste of money. If the space isn't going to be "conditioned", it isn't worth it.
But, since you're contemplating a re-roof look at using radiant barrier roof decking.
Over the years of countless house building those built with radiant barrier decking are 10-15 degrees cooler even when they're in the rough-in stage and no windows. Other than that, just keep it simple- good air flow with a passive system of soffit vents and ridge or gable vents.