On one of my first pilot recommendations as a new CFI, I sent a student to an examiner for a practical test with a messy, disorganized logbook (sorry Frank). The ensuing "paper chase" to validate his hours and experience wasted lots of time, made the applicant understandably nervous and the examiner irritated; what a bad way to begin a test! I was guilty of starting this person with a huge disadvantage on this important evaluation. To his credit, he passed this test with flying colors (and all susequent flight tests too). After this mistake, I was very careful to emphasize that every applicant should have a neat file with all the pilot paperwork available, the endorsements clearly marked, and the required aeronautical experience labeled and verified. Several good CFIs have prepared forms to copy in this information so the test gets off to a calm, professional start. Browse here for private, instrument or commercial forms that document all the required experience. If you have any doubt about what is required please check the appropriate regulation or this FAA provided aeronautical experience list. If the X-C was accomplished in another distant location, bringing the charts to show the routes is a good idea also.
Frequently pilots for advanced certificates and ratings are unsure what previous time can be "mined" out of the logbook. Can the X-C training time from private training be used for commercial? Usually for dual training, the answer is "no" but for experience "yes". The reason is that the regulation for the new certificate emphasizes that the pilot must receive training "at the commercial level" for the new certificate. What point would there be in allowing some previous (lower level) training to serve for what should be advanced commercial preparation? Questions of this sort should be resolved with the examiner before the appointment. Nothing wastes time and creates ill will faster than getting together for a much anticipated, long-awaited appointment only to realize that the test cannot proceed due to a lack of hours or experience. We just end up fishing around for another time when the plane the pilot and the examiner (and of course the weather) all can make another appointment. A good source for answers to complicated questions is John Lynch's FAQs. This is no longer regulatory but provides the spirit and intention of regulations and resolves gray areas. It sometimes is hard to find an FAA Inspector at work on the weekend so often this is where I have to go to get an answer in a pinch too. It usually is a better idea in each case to be "over-prepared" and have more than the minimum required experience.
CFR 61.29(a)4 adds a provision to the "solo" provision of the regulations which allow a flight instructor to be on board while logging solo time. Only the FAA could parse this. Here is the legal interpretation and if this is correctly logged it MUST be accepted by the pilot examiner. Another recent change of note: all tests the 60 day prior and discontinuance now is "two calendar months." See 61.39 prerequisites.