David Lewis said:
If enough time elapses, wouldn't eventually low man's calendar read Monday, and high man's calendar read Tuesday?
Not according to current conventions, no. Coordinate time and proper time are different, though closely related, entities, and that the calendar is based on coordinate time, not proper time. Note that the coordinate time is generally regarded as a convention. A less modern example of the conventional nature of the calendar is the difference between the Gregorian calendar and the Julian calendar. Usually there isn't much ambiguity anymore about what convention (calendar) to use, though this wasn't always the case. In ages past, I've read that different social agencies would use different time conventions (I don't have a reference for this handy,unfortunately), and historians would report important dates via several different conventions, such as who was in office at the time
Our modern realization of coordinate time is TAI, International Atomic TIme. In the modern system, it is recongizned that physical clocks, that keep proper time, tick at a different rate than coordinate clocks, which keep coordinate time. The difference in rate between coordinate clocks and the physical clocks is commonly referred to as "gravitational time dilation", the title of this thread.
TAI time started out by being an average of all clocks on Earth from participating institutions, but when the accuracy of our clocks became high enough, the averaging procedure was changed to recognize and account for the fact that clocks at different altitude tick at different rates. So the rate is adjusted by altitude, first - then the average is taken.
The coordinate time is based on the concept of the reference clock for the coordinate system being at sea level. This is a good enough system for now. The issue of the effect of solar and lunar tides and how that affects the very concept of "sea level" isn't currently important enough to be an issue, but may become an issue in the future as our timekeeping standards improve. The current paradigm is that all clocks at "sea level" tick at the same rate, and that sea level can be regarded as something static, indepenent of time, rather than something dynamic, dependent on time.
It may not be obvious at first glance how or why all clocks at sea level (ignoring tides) tick at the same rate, but references such as Wiki and (MTW's Gravitation) will support this claim.
A competing system, that avoids the whole sea level issue, puts the reference clock not at "sea level", but at the center of the earth. Unfortunately, this means that clocks on the Earth's surface don't keep coordinate time when this system used. This is barycentric coordinate time, TCB. It, or similar systems derived from it, are sometimes used for astronomy. This is an oversimplified overview, but it wouldn't be helpful to go into more detail at this point, and frankly I don't recall all the details offhand anymore.
https://en.wikipedia.org/w/index.php?title=International_Atomic_Time&oldid=917191735
wiki said:
In the 1970s, it became clear that the clocks participating in TAI were ticking at different rates due to
gravitational time dilation, and the combined TAI scale therefore corresponded to an average of the altitudes of the various clocks. Starting from Julian Date 2443144.5 (1 January 1977 00:00:00), corrections were applied to the output of all participating clocks, so that TAI would correspond to proper time at
mean sea level (the
geoid).