I don't have much patience for worn biking shorts... Over the years I've learned to plan on buying at least one new pair of shorts each year. This year I bought 2, and I have 2 pairs of older shorts that are still in a condition that I consider wearable. Four works, although it means in the summer that I can't get through a whole week without washing shorts. I wash them every time I wear them, and for the most part they go in the washer and the dryer.
When I tour, I only take 2 pairs of shorts with me. I wash the "worn" pair out at night, and if they don't dry overnight I still have a dry pair to wear while the damp ones are hanging from my trailer or panniers. So I suppose I could get by with less than 4 pairs of shorts that are in decent condition. But I really prefer to machine wash them.
With 4 pairs, I can generally get a couple of years on a pair of shorts. But when I rode my bike across the US, I had to replace my shorts in Colorado. Somehow 2 pairs of shorts just couldn't take the strain of being worn every other day, cycling all day long...



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