I'll take a crack at this:

1. Disingenuous: No, it's not disingenuous in any circumstance to consult an expert on the law, ensure your rights (few as they are) are protected, and ensure the regulatory agency correctly follows its regulations and statutes.

2. Undermines the Basic penalty System: I don't know what this means.

3. Costs money: It doesn't cost the government anything and if the case is complex it will save money. A lawyer is held to a higher standard than the pilot. The costs of missing filing deadlines, failing to preserve issues for appeal if required thus waiving them, failing to fully comply with reasonable requests falls on the lawyer and the lawyer will be sanctioned for unethical or incompetent behavior, and probably sued by the client as well.
If you're referring to the pilot, well, if he prevails then it is money well spent; if not, then he can sleep at night with full confidence that he completely understood the issue, his rights were protected, the process was correctly followed, and the penalty, if any, was fair.

4. Wastes everybody's time: I'm sorry, no. The regulator controls the process and time here. Do you mean it prevents the regulator from bullying a pilot into waiving rights and due process because the pilot doesn't understand the enforcement side of the law thus saving the regulator time by not having to provide fair and equitable due process? I'm sure that's not what you mean.
A lawyer will identify discrepancies or points of disagreement and clearly and efficiently identify those points so the regulator may quickly address and respond in the appropriate manner as they interpret the law. You mentioned technicalities above. I would be interested in learning what you consider a technicality. Failing to provide adequate notice (the certified letter) to the proper party at the proper address (the pilot's burden to keep that updated), failing to preserve evidence, failing to follow the C.F.R.s and local procedural rules, abuse of discretion, etc ... are not technicalities; they are violations of due process and an affront to fairness and freedom. If a regulatory agency cannot follow it's own rules, regardless of whether the violation happened or not, it cannot proceed with enforcement. Regulatory compliance is a two-way street.
Additionally, the process entitles the accused to a hearing and an appeal to the Administrator. Asking for the full process required by law be followed is not a waste of time, it's a right protected by regulation and statute. Statutes are intentionally vague and crafting regulations to accurately empower those statutes is tough. Sometimes the language the is misinterpreted by the agency and that interpretation does not fully contemplate congressional intent. Challenging agency interpretation of regulations is the only way to flesh out the meaning and operation of regulations. It makes good law better, and exposes weaknesses in bad law.

5. Does not make anyone a better pilot: Yes, I agree with you here. The adjudication phase is separate from the penalty phase. And no, it is not wrong to work with a lawyer in the penalty phase to ensure the agency does not overreach or punitively penalize the pilot for ensuring his rights were protected throughout the process.

Administrative law is designed to provide a fair, equitable, and consistent process over an infinite number of possible situations from the most minor to the most egregious. Competent and knowledgeable parties on both sides ensure the best outcomes.
For those of you who take a moral or "good character" approach to regulatory compliance and whether to retain counsel, your argument only has any relevance in the situation where the regulator does absolutely everything right, and the violator does everything wrong. A very rare circumstance indeed.
It matters not if the penalty for the violator is the same whether he "confesses" immediately or lawyers up first. (In fact it better not be any worse if he lawyers up first) There is no plea bargaining in administrative law and there should not be a trial tax either.


Administrative law changes frequently and can get convoluted and complex. If you read FAR's cover to cover every year on January 1, Great! Now how well do you know the statutes that enact the laws that the regulations provide the operational language? Do you even know where to find them? If you are an agency employee charged with enforcement, it is your foundational duty to know them well and be up to date on the changes.