Dear Ian,
I onjoyed reading your essay. Several of the issue that you discuss have been paradoxical for ages and have not been resolved satisfactory. There is, however, a way to get around those issues, which I will explain below by addressing them specifically.
1. Page 4. the second expression for the average speed makes the assumption that the limit can be determined, because dt (read d as Greek delta) can be made arbitrary small. This is not the case. As I describe in my essay, for electrons, dt has a lower bound equal to 10 exp (-20) sec. A The electron would cease its existence by 'making it smaller'. In other words, mathematically, one can determine the stated limit, but it is unphysical. The velocity of a massive particle is well-defined, even although dt is different from zero. The velocity of a particle does not need to be described in terms of a mathematical limit at all: a definition in terms of a discrete ratio is sufficient, i.e. v = dx/dt, where dx and dt are constrained by quantum condition (4) stated in my essay. In this way, an electron can be assigned a velocity without measuring this (see page 6 of your essay where you discuss the issues around this).
2. Page 5. Classical Light. I assume you mean light described in terms of classical theory.
3. Page 5. "by Brukner and Zeilinger to argue that the continuum is nothing but a mathematical construct, a view I wholeheartedly endorse". I do not necessarily agree with this view. As I describe in my essay, continuity needs to co-exist with discreteness. In the theory I describe, two underlying continuous fundamental fields are needed to explain the existence of particles, interaction between particles, and dynamically emergence of local discrete space and time.
4. Page 5. "So what happens in the limit as dt --> 0 for classical light?" As I indicated under 1., dt cannot be smaller than 10 exp (-20) sec. Light cannot be attributed a discrete time, unless one wants to define it as wavelength/c. The latter is not very useful, since the time would be wavelength dependent.
5. Page 5. "Suppose we decrease dt while leaving dx unchanged. As dt gets smaller and smaller, it implies we are measuring the difference between x1 and x2 more and more rapidly. Lest we forget, classical physics limits how rapidly information can propagate. At some point, without changing dx, we will be empirically prevented from further reducing dt since the ratio of dx to dt cannot exceed the speed of light. So, if we wish to take dt --> 0, we must take dx--> 0 in order to keep the ratio at or below the speed of light."
There is an implicit assumption made that dt can be made arbitrary small, which is not the case as I explained earlier. For a stationary electron dx=0, while dt=10 exp (-20) sec, such that the ratio dx/dt=0 and there is no issue with violating the speed-of-light as one would get by assuming that dt can be made arbitrary small. When the speed of an electron increases, both dx and dt increase, but their ratio cannot exceed the speed-of-light c. In my essay, I explain that this is due to the fact that the internal speed of random spatial motion of an electron is equal to the speed-of-light. The details can be found in the second report on my website.
6. Page 5. "The classical theory of light assumes light is a wave which is an inherently non-local phenomenon". Indeed. This result in a paradoxical behavior. However, is is also known that light consists of photons, which propagate at the speed-of-light, and posses a kind of corpuscular behavior when detected. When one assumes that photons are oscillating blobs, then they do not behave as a classical wave. Still, a 'wavelength' can be assigned, which is equal to the length of the oscillation.
I have a few more comments, which I may write up later.