Since frankly I'm not smart enough to determine on my own what is "illegal but safe" in every given situation,
Neither am I. But that doesn't mean that you are
always not smart enough to know whats "illegal but safe".
thankfully the work has been done for me through the manuals, placards, and limitations that I'm required to comply with--and since I'm going to do it "by the book", I don't have to worry about taking unnecessary risk.
If you always go by the book 100% of the time, you are not necessairly guaranteed safety from "unnecessary risk" 100% of the time. The point I'm trying to make is that there is no one to one link relationship between safety and legality. Flying an ILS down to minimums creates "unnecessary risk" in some situations if there is another airport within fuel distance that doesn't require going down to mins. If you want to never stray from the book, then thats great. But don't be fooled into thinking thats the only way to guarantee safety.
Can certain rules be waived while achieving an equivalent level of safety? Absolutely! Look at your minimum equipment list (if you've ever seen one before). Rarely is everything working 100% on the C-5s that I fly, but I have official guidance in the form of an MEL that tells me under what conditions I can safely depart with malfunctioning equipment. For example, normally we're required to have an operational weather radar, but suppose it happens to be broken today; I pull out the MEL and it says I can go as long as no portion of my route will take me into areas of known or forecast thunderstorm activity (control measure). Then I also look over and the co-pilot's radar altimeter is busted; I look that one up also and determine it's okay to go as long as I don't do a CAT II ILS. Other rules may be subject to waiver also, but there's always another set of eyes in the form of a waiver authority who is looking at what rule you request to waive and why it is necessary to waive it; this person does a cost-benefit/ORM analysis to determine under what conditions he will grant the waiver to mitigate the risk, by looking at factors such as weather, the priority of the mission, the experience level of the crew, the crew's duty day, etc. Unnecessary risk will be avoided; necessary risk will be mitigated. And I can guarantee you nobody is going to grant me a waiver to do an aileron roll in a C-5 because 1) it's not necessary to achieve any mission objective, 2) the risk is not justified by the potential benefits, and 3) my loadmaster will probably shoot me first.
All those things you posted I agree with. But I'm not talking about flying into thunderstorms without weather radar, or anything like that. I'm talking about doing a maneuver, when done correctly, puts less stress on the airframe than a steep turn. Sure there are dozens of things that could occur during doing a barrel roll that could cause an unsafe situation. If and only if every one of those factors are dealt with accordingly can the maneuver be performed safely. Some of those factors include pilot skill, aircraft condition, aircraft weight, whether you're on a IFR flight plan (loss of altitude may cause an altitude violation), the list goes on.
You (and just about everyone else in this thread) seem to hold the belief that if it's illegal, its impossible to do safely. My belief is that if it's illegal, its unsafe to do
unless you go above and beyond the "normal call of duty" to ensure you're being safe. That may mean looking through aircraft logbooks to ensure proper maintenance, or pulling a stick shaker circuit breaker, etc. but it is certainly
possible.
More on the legality aspect: In general (as in non-aviation realms) legality is looked upon with a "do it, but don't get caught and don't hurt anyone" mentality. No one condemns drivers who go 60 in a 55 zone, as long as no one was put into dangers way (and it doesn't take a Formula One-trained test driver to properly determine if the 5mph excess speed is going to put anyone in danger or not). No one foams at the mouth at the mention of 19 and 20 year olds drinking as long as they're not driving or putting themselves in an alcohol-induced coma. No one chimps out about downloading MP3's or movies from the pirate bay. No one ever feels the burning need need to run to the police when they hear of someone else smuggling into the US a Cuban cigar or two for personal use...
So tell me, why do people get so worked up over someone committing a "crime" in an airplane when no one was hurt or put as risk?