From your original post, you wanted to "quantify how closely the run order approximates true randomization".
You tell me what true randomization looks like and I could probably find a way to quantify how close I am to it.
Ultimately, randomization of the DOE runs is like an insurance policy against unknown/unexpected error sources that could be related to time or the order that the experiments are conducted. Those error sources, if present, would manifest themselves in the response data that is collected which is why @Victor_G provided that insight.
As long as a reputable random number generator is used (which JMP does have reputable random number generators), any random pattern is typically appropriate. Specific situations may indicate that it is NOT, but you would need to know those specific situations.
For example, suppose a piece of equipment will always make a mistake on the fourth item that is produced. In that situation, a valid random pattern just might put one of the factors at the high setting every fourth time. For an 8 run design, that would be very plausible. But that would certainly influence the results. You would not know that until conducting the analysis and then, most importantly, when VERIFYING the results. I have seen something similar to this happen in the real world in spite of a "valid" random pattern.
Finally, the statistical analysis and properties that you ask about assume that the error terms from the model are independent and identically distributed. Manually reordering the runs of a DOE should not affect that. In fact, you do not even need to randomize, if you know that each run is truly independent. Most people randomize to act as an insurance policy against those unknown error sources (as mentioned above). If manually moving design runs affects the independence, then your design (and analysis) should take those time features into account.
I hope this information helps. And remember, all experiments should be verified and even the sequence 1, 2, 3, 4, 5 is a possible random pattern!
Dan Obermiller