A few thoughts on the idea of "plain language" regulations:
1) Regulations *are* plain language. They are written in English. some of the words may not be very commonly used in general usage but they are all English. I don't recall ever seeing latin words used in the regulations. Any word you find in a regulation, you will find in a dictionary. Occasionaly a word in a more liberal dictionary (yes there are liberal and conservative dictionaries) will have several definitions of a word which are diverse enough to cloud the meaning of a regulation containing that word. In such a case, you should take a look at a legal dictionary for the meaning of the word when used in a legal sense. Now, you may say, "well if you need a special dictionary, it is not "plain language"". Well yes and no. In law, words have specific meanings, whereas in general use those words may have many meanings. But, this is no different than any other field of specific knowledge. Take aerodynamics. What does the word "chord" mean? In common usage Chord, has many meanings, in aerodynamics it has only one specific meaning. In order to understand aerodynamics, you have to know what is meant by the word "chord" in hte context of aerodynamics. In engineering "stress" and "strain" have very specific meanings and they are not interchangeable, wheras in common usage those two words are used in many different ways and often are used synonymously. To understand an engineering report, you have to know what the engineering definition of "stress" and "strain" are. Law is no different, you have to know specifically what is meant by "notwithstanding"
2) Like Avbug said, many of the misunderstandings of the regulations come because pilots just don't read them. You gotta read them. It doesn't do any good for the book to sit on your shelf, or under your pillow at night, or wherever; you have to open the book and read the words. I see this time and time again on these forums. People ask questions that are better answered by opening the book and reading what it says. Inevitabley, you get 6 different answers, all of them incorrect, because the guys answering the question don't read the book either. People would rather have someone else tell them what something means instead of reading it themselves.
3) Many of the regulations which are beleived to be "grey areas" or "unclear" are not "grey" in the least, they are very black and white, but people don't like what they mean, so they prefer to believe that there is a "grey area" A classic example is logging SIC in a single pilot airplane. The regulation is pretty d amn clear; the SIC has to be required by the regulations. But, people don't like that , so they say .... "wellll, "regulation" really means "insurance requirements" no, it doesn't, it means "regulations"; or " regulations really means company policy". No it doesn't, "regulations" means regulations. However clear this may be, it is clouded by people attempting to "interpret" it to mean something it clearly doesn't mean to further their own agenda.
4) "Regulations are written in a way that is hard to understand." Perhaps, perhaps not. I'll agree, often the syntax is clunkey and hard to follow. The sentences do not flow like conversational sentences. The thing is, it is very difficult to impart specific, detailed meaning in a conversational manner. You can't have regulations that read like a novel, and have them impart the same specific, detailed, meaning. In order to read a regulation for understanding, you have to read it carefully, think about the meaning of each phrase, and add the meaning of each phrase together to get the meaning of the sentence. The regulations has to say "exactly" what it means. Take for example the previously mentioned regulation on passengers in a pilot seat:
§ 135.113 Passenger occupancy of pilot seat. No certificate holder may operate an aircraft type certificated after October 15, 1971, that has a passenger seating configuration, excluding any pilot seat, of more than eight seats if any person other than the pilot in command, a second in command, a company check airman, or an authorized representative of the Administrator, the National Transportation Safety Board, or the United States Postal Service occupies a pilot seat.
Yeah, it would be really nice if it just said something simple like: "No passenger shall sit in a pilot seat." Nice, but the thing is, there's a world of difference in what those two sentences mean. First problem is; what is a passenger? Is a postal inspector a passenger? maybe is a fed on surveillance a passenger? Maybe. Pretty soon you see that it is easier who specify who *may* occupy a pilot seat, rather than who *may not* sooo.... we say "only a pilot or a fed may sit in a pilot seat in flight" OK does that mean that a passenger with a private pilot certificate can sit in a pilot seat? well no, so we have to specify the pilot in command or second in command .... uh-oh, what about a check airman giving a line check? He's not a PIC or SIC ... so we have to add that to the list.
So we start out with "No passenger" and very quickly we end up with: "any person other than the pilot in command, a second in command, a company check airman, or an authorized representative of the Administrator, the National Transportation Safety Board, or the United States Postal Service"
Ok, how about this item: "aircraft type certificated after October 15, 1971, that has a passenger seating configuration, excluding any pilot seat, of more than eight seats"
now, for whatever reason, it has been decided that this restriction applies to a) aircraft type certificated after Oct 15, 1971,
and
b) aircraft with more than 8 seats, not counting pilot seats.
I don't know why this is so, but remember, we are discussing the "form" of the regulations, not the "content" That in mind, I would invite anyone to take a stab at writing something in "plain language" which is simpler and less awkward, which still clearly communicates both a) and b).
Lastly, there's accountability; who does the regulation apply to? who do you charge with hte violation? If the regualtion says "no passenger shall..." the regulation applies to the passenger's actions. There's a violation, the FAA begins an enforcement against the certificate holder for violation 135.113, the certificate holder says; Hey this reg applies to passengers, we're not passengers, bring your enforcement avgainst the passenger, he's the one who violated the regulation" .. and the certificate holder is right. SO the regulation is written "No certificate holder may operate an aircraft ...." which makes it clear that it is applicable to the certificate holder's actions. Again, it doesn't read like a novel, but there's a real reason that it's phrased that way.
Yes the regulations are tougher to read than Louis Lamour, but that's going to be inherent. Louis Lamour isn't trying to write specific detailed instruction which do not leave loopholes. Regulations require reading for comprehension, you can't just skim them and pick up the "drift" like you can with cowboy novels.
I'll expand my previous challenge to include all of the aviation regulations. Take any regulation from CFR 14, and re-write it so that your version imparts the exact same meaning as the original, yet is easier to read and understand. Post the original and your version. Seriously; try it. I think the experience would be revealing. Sure there are a few which could be perhaps a little more readable, but I think that by and large you will find that the regulations have to be written the way they are in order to mean what they must.