Maybe the vacuum is not bleeding off the shut off valve on the first try. Pull the hose off the shut off valve manually and see if it starts on the first try.

__________________
1977 300d 70k--sold 08
1985 300TD 185k+
1984 307d 126k--sold 8/03
1985 409d 65k--sold 06
1984 300SD 315k--daughter's car
1979 300SD 122k--sold 2/11
1999 Fuso FG Expedition Camper
1993 GMC Sierra 6.5 TD 4x4
1982 Bluebird Wanderlodge CAT 3208--Sold 2/13

X2
Could be the vac switch on the ignition switch is on the way out or a tube is kinked or blocked.
It would not hurt to test your GP's as well.

__________________
Grumpy Old Diesel Owners Club group

I no longer question authority, I annoy authority. More effect, less effort....

1967 230-6 auto parts car. rust bucket.
1980 300D now parts car 800k miles
1984 300D 500k miles
1987 250td 160k miles English import
2001 jeep turbo diesel 130k miles
1998 jeep tdi ~ followed me home. Needs a turbo.
1968 Ford F750 truck. 6-354 diesel conversion.
Other toys ~J.D.,Cat & GM ~ mainly earth moving