I would think if he was pumping the brakes to get them to work that it wouldn't point to a torn diaphragm since the act of pumping the brakes effectively bleeds out any vacuum stored in the booster itself.
And, yes at highway speeds, there is less vacuum pressure available, but there is also more vacuum volume available. And if you're on the highway, practically the last thing you do before hitting the brakes is lift off the gas pedal, which in turn raises the vacuum pressure, even if for a second or two, which should 'refill' the booster almost instantly.
I would lean more towards something like the fact that the fluid might've gotten low at one time or another and now there's a bunch of air in the lines somewhere and the brakes need to be bled out.
The other case I'd lean towards is a bad primary piston seal in the master cylinder...which will cause the pedal to fall until it's 'tagged' once or twice, enough to get the o-ring to flare out a bit and make a good seal.
Start the engine, let it idle for a minute or two, shut the engine off, let it sit for a few minutes. Do you hear a hissing coming from the brake booster? If so, is it coming from inside the booster or from the hose going into the booster? If it's inside, you need a new booster, no question. If it's the hose, you might have a bad check valve.
After a few minutes (5-10-15, whatever) have gone by, get in the car and step on the brakes (full stroke) a few times. Does the brake pedal get progressively harder or is it hard from the first push? If it gets harder and harder with each push, the brake booster is likely good, but you might have air in the lines or have a bad primary piston seal (i.e. need new master cylinder).
After you've pumped the brake pedal a dozen times or so until it's good and hard, let it sit for a few more minutes (5-10 whatever), then push on the pedal fairly hard and hold it. If it drops to a certain point and sits there, then the master cylinder is likely good. If it drops to a certain point and then slowly drops to the floor, the primary piston seal in your master cylinder is likely bad and you'll need that new master cylinder. If it sinks to the floor on the first push, you've probably got air in the lines and need to bleed the brakes completely.
Got all that? My fingers are pooped...