Trip passes were issued by all RR’s and provided to employees of other railroads, usually just for “official” business.  If you were traveling on personal business/vacation and weren’t eligible for a trip pass, you could get a half-rate order (i.e., the foreign road would charge you one-half of the regular rate; Pullman accommodations had to be paid in full).

Trip passes were for a single trip (usually a round trip).  On completion, the conductor would take up the pass and turn it in to the auditor with his other lifted tickets. Annual passes were just that, good for an entire year (sometimes more to save the cost of issuing annually to long-time employees).  The bearer would just flash the pass and the ride was free.  The conductor did not take the pass and, once expired, the bearer could keep it or toss it. 

Annual passes were given to selected employees and their families as well as to certain foreign road employees of significant position.  Senior retirees often were given lifetime passes, as you’ve posted.  Many passes were restricted to prohibit use on key named trains (as can be noted on the 1943 PRR pass you’ve posted).  Pullman also issued passes for accommodations but they went, usually, to senior managers only unless sleepers were needed in carrying out a particular job. 

I (and my wife) did a LOT of traveling on half-rate orders all over the US when I was on military leave from the LIRR.  When I was actively working and carrying my LIRR pass, most (not all) foreign conductors would honor the LIRR pass for a coach ride.  My best “score” on that account was a free ride on the Erie-Lackawanna from Hoboken to Chicago on the Lake Cities.  Lots of trips on PRR name trains from NY to Philadelphia.  PRSL and the IC would NEVER take my pass. Archive/Info: Brad Phillips

trip-pass_Carpenter_Penn-Yaphank_11-21.jpg (101318 bytes)
Trip Pass Carpenter NY to Yaphank 11/1921
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Trip Pass Trainman Sag Harbor to Jamaica 12/1928
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Trip Pass Trainman Sag Harbor to Jamaica 12/1928
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Trip Pass Block Operator Jamaica to NY 7/1930
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Trip Pass Highway Watchman  Stuart Manor to Jamaica 12/1934
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Annual Pass Extra Clerk over entire system 1936
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PRR Annual Pass for retired LIRR Engineman over entire system 1943
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Trip Pass for daughters of ticket clerk Patchogue to NY 10/1953 Archive: Dave Keller
trip-pass_UPRR-Livestock-Agent_NY-Port-Jefferson_5-1950.jpg (74608 bytes)
Trip Pass UP RR Livestock Agent  - Port Jefferson to NY 5/1950
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Trip Pass UP RR Livestock Agent  - NY to Port Jefferson 5/1950
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Trip Pass Son of Block operator Port-Jefferson to NY 12/1942
trip-pass_Agent_1955-56.jpg (84560 bytes)
Annual Pass Agent "20 years of service" 
entire system 1955-56
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Annual Pass Wife of Agent "20 years of service" entire system 1955-56
reduced rate order Massapequa 12-1958.jpg (98235 bytes)
Reduced Rate Order Massapequa to NY 12/1958
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Annual Pass lifetime - retired engineer  
Dashing Dan
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Annual Pass lifetime - Wife of retired engineer  Dashing Dan
trip pass wife clerk Brad Phillips NY-Amityville_9-1971.jpg (55537 bytes)
Trip Pass Wife of Clerk Brad Phillips NY to Amityville 9/1971

Retired LIRR Ticket Clerk Thomas Bayles took me on a coach trip to Bridgeport, CT about 1967 or 68. He carried me on his LIRR pass into Penn Station and when we got our connection from GCT on the New Haven, he had the option to show the conductor either his LIRR pass or his Pennsy pass, which he was also issued. 

He opted to show his LIRR pass and we got to ride free.  The conductor said to him "Good thing you didn't show me a Pennsy pass. . I'd have thrown you off the train." Obviously the conductor wasn't afforded a free ride on the Pennsy sometime back using his New Haven pass. . . . and he was about to return the favor. Info: Dave Keller