I've spent 35 years working within Transport Canada's airworthiness regulatory system, and by osmosis, the FAA system. With my less complete understanding of the UK CAA system. I can see that Transport Canada's system was initially inspired by a combination of our UK heritage, and a largely military origin. Over the recent decades, we in industry have been able to convince Transport Canada that many of the more burdensome military origin regulations were excessive, and did not improve safety, and they have been removed or dialed back.
It is apparent to me that the FAA system was more a product of the US government wanting to get as many citizens flying planes as possible after WW2. Thus, things were made reasonably easy, imposing regulations only where there was a clear need for them. From my UK heritage, it seemed more apparent that flying and airplane ownership in the UK was somewhat more reserved for a certain segment of society - who could afford a military type operation for their aircraft.
Due to ICAO privileges, ICAO compliant aircraft are generally welcomed in other nation's airspace, though must be operated to also respect their rules. I have flown Canadian registered aircraft in the US, Caribbean, Scandinavia and Europe, and always felt very welcomed. But, while outside Canada, I try to behave like a guest in airspace, rather than flying by entitlement, as I do in Canada. One of my planes is a Canadian "Owner Maintenance" aircraft, which though type certified, I have voluntarily removed from having a full C of A. As such, it is not accepted in any other nation, so may never leave Canada - it's okay, Canada has lots of room to fly, it does not need to leave!
In my opinion, an obvious decline in private GA ownership, and recreational flying will reduce any momentum to further ease the regulatory structure. Transport Canada staff have told me that they would welcome a regulatory change to greatly simplify the operation (mostly maintenance and modification) of light GA aircraft, but there is just not enough resource to dedicate to creating the regulatory change (which means that there are not enough taxpayers insisting that government time be spent on that). The regulatory structure to maintain a GA plane has eased toward less burdensome and found a "happy place", though modification is still overly burdensome.
For those people who can lobby their regulator for simpler regulation around GA aviation, excellent! But as the staff of the regulator naturally turns over by retirement and hiring, what is happening is that the new hires who are coming to regulate our aircraft are no longer the old, experienced, relaxed ex military people who apply their wisdom, and let things succeed, but rather, new university graduates of business, engineering, or administrative disciplines. They do not have the self confidence to just apply a light touch to a request for change, but will instead dive headlong into understanding every corner of it - if the boss allows the dedication of resource. And, you gotta know, that the Boeing 737 Max 8 goings on are going to intensify the trend toward more intensive review of everything, aircraft certification is not going to ease up for a while! If the regulator cannot afford the resource for the new, less industry experienced staff member to wholly understand, that person will be reluctant, and things will languish - as long as the citizen applicant tolerates it! Literally, a couple of my projects with Transport Canada have stopped, simply because my client died while waiting for a delayed project to advance through the system.
From my perspective, we in GA right now, best get used to working in whatever system we have. Yes, we may affect change, though by the time change is effective, it'll be for the next generation more than us!