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I think it’s a fascinating theory but I think it would require extraordinary skill and even more extraordinary luck to pull off.

On top of the skill of performing the shadowing maneuver, the Flight 370 pilot would also need to know the precise location, altitude, and heading of the Singapore Flight to make the rendezvous and assume the proper tailing position. He’d have to match speed, maintain position, and shadow the moves of his target without ever communicating with it, in the dark, with no known night-vision equipment to assist him.

The Singapore flight has it’s transponder on, suction cup a directional antenna to the windshield and put a signal meter on your thigh, then just fly the plane at the Singapore flight transponder. (Just like finding a bear/wolf/shark with a radio collar on animal planet TV.). The Singapore flight is lit up like a Christmas tree, you might easily see it at 20 miles, 50 with binoculars.

Why would you need night vision? Just follow the navigation lights.

I can’t speak to the skill of tailing another plane that closely, but everything else doesn’t seem like a high hurtle.

Ultimately, this doesn’t seem plausible, but it’s not beyond the pale.
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"He’d have to match speed, maintain position, and shadow the moves of his target without ever communicating with it, in the dark, with no known night-vision equipment to assist him."

I was thinking about this aspect of this theory as well, and certainly, the Malaysia Air pilot would not have been able to mind read the lead pilot, but as far as the distance and position, there would be a very rudimentary solution to this. In WWII, the Lancaster pilots who flew the dam buster missions had to be as close as possible to an altitude of 60' above the water for their drum bombs to skip to target. Altimeters at the time were not that precise so theater spotlights were fixed to the bottom of the fuselage, one up front and one towards the rear, and were angled to converge at 60'. The aircrews knew if they saw two beams they were either too low or too high, but when the spots merged they were just right. One could similarly use green lasers angled to converge at virtually any desired distance one needed them too, and make a simple bracket with two laser pointers that could be mounted inside the trail plane's windshields and visually maintain a precise interval behind and above another airliner...