what's your take on this reg?

From a philosophical point of view, I agree with the examiner. The intent of the rule is that you should have night VFR cross-country experience. Flying under the hood on instruments at night does not require the same set of skills as flying it visually. If you were my student I would have made you do at least a 100 mile night cross country (200 mile round trip) without benefit of electronic navigation and maybe without benefit of any gyro instruments at all. How can you consider yourself to be a competent commercial pilot if you've never done something like that? The time to learn is not when you have paying passengers aboard.

However, from a regulatory standpoint, I cannot agree with the examiner that your night instrument cross-country doesn't count because the regulation now says in "nightime conditions" instead of "in night VFR conditions", which is how it used to be worded. I believe that changed in 2009, so perhaps the examiner wasn't looking at the latest copt of the regs, but I find that a little hard to swallow. At risk of making her angry you could appeal to the local FSDO for a ruling and it might go in your favor, but as a consequence your flight test might turn out to be harder.

My interpretation is that the paragraph (3) section (iv) requirement also has to be dual, exactly as the Bizjet gentleman has pointed out regarding the definition of "training".

In the end, experience is what counts and you undoubtedly need hours anyway to get a job. Suck it up and go do a real VFR night cross country flight. Do it exactly how I suggested, without benefit of navaids. If you're a real man, you'll go someplace you've never bween before, you'll do it on a moonless night, you'll wait until long after sundown before takeoff and you'll cover up the DG and AI and just leave yourself the turn coordinator and magnetic compass. For fun, go 500 miles that way at night, one way. I have many times.

Part two is easy: yes, it must be made with an instructor.

FAR 61.1:

(6) Flight training means that training, other than ground training, received from an authorized instructor in flight in an aircraft.

(18) Training time means training received—

(i) In flight from an authorized instructor;

(ii) On the ground from an authorized instructor; or

(iii) In a flight simulator or flight training device from an authorized instructor.

The first part of your question is not as straight forward. The argument that I've always heard is that the training time specifically required for a certificate has to be training toward THAT certificate. Your long instrument XC was part of the training for the instrument certificate. It can be counted toward total aeronautical experience, but cannot be counted as one of the specific training requirements for an additional certification.

I'll edit this post if I can find specific guidance on that.

to addition what been dere dun dat said, i will throw some stone age pilot knowledge.

The nighttime IFR is really different from the day one, agree?

Now nighttime VFR is very different from day VFR. the terrain looks differently, there are different terrain features visible, and it provides a whole lot of challenge.

Do your night VFR so that one f*g night when all your nav gadgets take a break, you will be able to bring that blackout cockpit and all it is attached to back to the ground safely.

Your interpretation of a regulation isn't important or even relevant. The examiners interpretation is the only one that counts. Right or wrong.

The nice folks at the IRS, and helpful and flexible compared to the FAA. They are always right even when they are wrong, and don't forget it.