Dissecting "I'd Be Better Off (in a Pine Box)" by Doug Stone - 1990

Doug Stone takes us down the pit with him in this monument to country self-pity: 1990's "I'd Be Better Off (in a Pine Box)". Stone showcases his vocals in this all-time classic downer, but how specifically do his phrasing and range augment the supremely depressing mood, and just what was in the look that, once received, shattered the glass for this protagonist with such finality?