3 could be a .45 NAACO, North American Arms Corp. LTD. Introduced in 1959 in Canada. Original rounds made from 7.62 NATO cases without hs. Also known as 11X30.4 mm. Information from Manual of Pistol and Revolver Cartridges by Jakob Brandt
I believe #3 is a Military .45 acp shot shell that has had the neck area straightened and reloaded with a .45 caliber bullet. Seen scans of one of these cartridges in my collection.
Case mouth dia. = .441’‘
Base dia. = .471’‘
Rim dia. = .472’‘
Case Length = 1.254’’
I think #1 is maybe a .22 newton.
As a recovering wildcatter I’d venture a guess that #1 may be a 22-4000 Schnerring. It would take a closer examination because it is nearly identical to the 22 Newton. The Newton usually used heavier, larger diameter bullets although it can be found with the lighter bullets used in the Schnerring.
Both cartridges were wildcats so it would be normal to find slight differences in dimensions because chamber reamers were almost always custom made.
I’d say that both have an equal value although I haven’t been following wildcats for several years so what do I know.