The Fed Law requires annual qualification to the standards of either the state issuing the credentials or the state you live in (for retirees) . . . yet MA CMR PROHIBITS any MSP LEOSA Certified Instructor from qualifying ANYONE other than a active/retiree from a MA Municipal or MA SP agency, so you would never be able to qualify in MA . . . and thus would not be compliant with LEOSA unless you traveled to Montana annually.
Not if Montana licensed persons who are not MA LEOSA certified instructors from performing the qualification. LEOSA states "to the standard of", not "in the state of".
Games like this that attempt to outsmart the intent of the law rarely succeed. It doesn't really matter what the clear plain language of the law means - the government (courts) will decide it means something else; change it, or simply adopt a policy that everyone who attempts to use this technique will have to fund a trial. LEOSA was "improved" in only a few short years under an anti-gun president. My guess is one year, two tops, before a loophole like this is legislatively closed in the event the court uphold that such purchases LEOSA status is valid. The only way "back door" LEOSA status will work is if persons in power use it to do favors for special, highly placed people - not as a de-facto national CCW for ordinary folk.
The chances the courts would accept that someone paying $1000 in return for which they received a $1 salary and special privileges was actually "employed" are also slim.
This sort of game is not much different than the state of MA declaring that any location with an internet connection is an "educational institution" since that connection can be used to complete credit granting courses from accredited degree granting institutions, and therefore require carry permission from said institutions.
If you look at LEOSA's requirements (original and current), much of it appears to be an attempt to preclude people from gaming the system and limiting it to legitimate career law enforcement officers - hence requirements like "pension eligible" in the original verison; 15 (now 10) year requirements for retiree status; "employed" rather than "sworn" status; etc.
One example of the govt shutting down creative parsing of the law is the old Michigan permit system that recognized non-resident licenses, but didn't specify "for non-residents only". Before MI permit reform, only persons of privilege, power and influence could obtain a resident permit. So, guess what? Some MI residents got creative and started mail ordering FL permits that clearly were valid (in fact, I think a MI legislator suggested it on the floor when arguing for permit reform). The AG's office declared non-resident permits invalid in MI claiming a non-gun decision that contained the wording "the law shall not be interpreted to imply an absurdity" meant that resident permits were invalid since bypassing the "special people only" procedure of MI law for residents would be absurd. I don't know if any prosecutions were brought against MI residents using out of state permits, but the AG's position was that charges should be filed against such persons.