135.293... 1 yr Initial/Recurrent (EQUIPMENT) check.
135.297... 6 month Instrument (PROFICIENCY) check.
135.299... 1 yr Line check: (ROUTES & AIRPORTS) Check.
...Seems to me with multiple aircraft under your belt, the FAA and any Certificate Holder you would fly for has ample opportunity to.. "evaluate someone as PIC".
When you dive into .299 in its current form and the background on its inception, its justification is elementary when you consider how easily the requirements of each paragraph are satisfied during the normal course of the 293 and 297 checks. The problem occurs for On Demand Operators who are required to operate to outlying airports during the course of EXCESSIVE appeasement of this section for EVERY Aircraft the Pilot is qualified to ACT as PIC. Many FSDO's interprit (a)(3) to mean "an airport OTHER than where the flight check originates." This creates a significant consumption of the aircraft and pilot(s) for airports not near an airway or additionally suitable airport(s) for the type of aircraft being checked.
There has been significant speculation of the FAA's rewrite of 135 to include deleting this section as it was originally intended for scheduled commuters, whereby the 299 flight checks could be conducted during scheduled revenue operations. Now it serves a dual purpose in that with todays simulator quality and realism, Authorized "Factory" Schools can, and do conduct all parts of 293 and 297 in many of these aircraft. 299 allows the FAA to maintain control and hands on surveillance of operators' PIC's by requiring "[route checks]...IN ONE OF THE TYPES of aircraft...". There is not a lot of wiggle room in thi paragraph for "simulator" or "representative aircraft". Removal of 299 from the regs would take the FSDO out of the cockpit of On Demand Operators for which Flight training and checks could be accomplished entirely within the 142 Simulator. Never gonna happen. There is nothing in writing to permit an inspector to "require" a 299 for every aircraft nor for each certificate the pilot is authorized to fly on. If an operator chooses to conduct this check with their own Check Pilot, and maintain the pilot's records, so be it. Many will proprieterize that check internally, so be it. However, they are required to file the results of each check with the FSDO who then records that against your airman certificate. You then have free access to the 8410 via Airman Records request.
POI's demanding compliance on a reg that does not exist sets a dangerous precedence. Local FSDO Mgmt should be appealed for relief. If not there, then the Regional level. No Joy there. FAA Counsel ought to be warned of the practice by your legal counsel for damages. That should just about do the trick. I am guessing the FSDO Manager has a loose cannon in the office and no one has squeaked uncle yet. Done deal after that. Retaliation by the POI. Most of the Power Tools from the 90's have been weeded out by the new customer service initiatives. An appeal process to the MGR should dissway retaliation if the guy wants to continue to be a POI. Besides, Pay is pretty good these days with the trimmed staffs, these guys are making a bit more than normal GS levels with the increased workload from the hiring freezes.
100-1/2