I am prepared to share some of my views with regard to your questions, but before I do this let me say that I believe this whole affair does not seem to be one of a genuine concern for “correctness”.
As the canons say, and as common sense dictates, the credibility of a person offering advice or any other kind of witness should be the first thing that is examined. This is what is done in any court across America, and whether one wants to admit it or not, this is what most people do.
So for me, anything coming from Gregory has to be seen in light of his history. He was very vividly described early in his endeavors by Fr. Panteleimon, who was responding to accusations made even then by Gregory’s few supporters. This testimony of course should naturally be held with equal suspicion until it is either credited or discredited with other facts. It seems to me the information that has since been presented has done nothing other than to lend a great deal of credibility to this letter, which by the way, has never been refuted or addressed in all of the many self-justifications coming from the Skete.
This letter of Fr. Panteleimon describes a reckless self-will, self-justification, and an unhealthy desire for clerical promotion (which has even been admitted by his followers recently), that has formed the basis of and driven Gregory into and out of every synod (or in the case of ROCOR, monastery) he has been in. In fact, I can adequately illustrate that all of the scandals in the Synod of Chrysostomos II and the Lamians centered on promotion to the episcopacy. It seems likely and reasonable then to think that his many recent accusations of the ROAC is sand thrown up in everyones eyes, to hide the real frustration of being restricted to Colorado (an embarrassment to someone who is power hungry) and thwarted in his efforts to have all of America as his territory.
Also lending support to Fr. Panteleimon’s letter, which also describes thievery, is Gregory’s fascination with material possessions. Clearly Gregory is deeply fascinated with the supposed “arrest” of Met. Valentine for “smuggling” money, lawsuits to gain money, and withholding other peoples property.
So before your questions can be answered Seraphim, I believe everyone must inform themselves of the history, most of which has not been covered here, and answer this: is this the work of a righteous man or a deviant personality disorder?
Now, to specifically address your questions.
With regard to Gregory’s discretion on how to receive people from other Old-Calendar groups. This is not a question on if an individual bishop can exercise discretion, it is a question of whether that discretion makes unnecessary, avoidable, and premature declarations on behalf of all the other bishops. Clearly a Mathewite at least has the form of an Orthodox Baptism. So if Gregory wants to believe they have the Baptism or not is perhaps at his discretion, but to re-baptize is to go out of your way to make a declaration. It is very irresponsible and prideful (imho) to think one can independtly make declarations for all your fellow bishops.
Now you might offer some counter-points here, but the bottom line is this: If Gregory’s position on who was “Orthodox” and was not was of such a vital importance to him that he could not exercise economia and insisted on his unilateral declarations, then it is totally inexcusable that he joined their synod in the first place. I might offer a quote from Fr. Panteleimon’s letter: “It is not we who have changed, it is you.”
Regarding the "Haiti situation". I might well agree that Gregory is correct. The Russians have been rather loose in their reception of converts for a few centuries and it was no different with the ROCOR in Gregory’s time. So if I, who am just a layman, know this, then how much more is Gregory responsible for knowing this also? Did the Church in all of these centuries ever consider this errant practice a cause to break communion and make grave declarations?
While Gregory may be right in this case (and I think he is correct), I contend he knew about Russian practice from his own experience in reading and his time in the ROCOR, and is now just using this as a “sand in the eyes” tactic.