1. Libraries treat dates as proleptic Gregorian
"A date object represents a date (year, month and day) in an idealized calendar, the current Gregorian calendar indefinitely extended in both directions." — flotzam
2. Calendar gaps create “impossible” dates that must be handled
"I assume there is a way to handle this in modern contract law. Surely people have forgotten how long the various months are and written contracts referring to April 31." — madcaptenor
3. Calendar adoption varied by region, so multiple systems coexisted
"Technically, they switched to the Revised Julian calendar, not the Gregorian. Also, it was only some of the churches making up Eastern Orthodoxy that switched; others remain on the Julian calendar to this day..." — jaculabilis