Was this the pre-historic beginning of the re-issue culture then?
yes and no. here is my longwinded answer...
doo wop collectors probably started the reissue/bootleg market, as early as the early 60's... somewhere out there is a great article about about Times Square Records and the 5 sharps record "stormy weather", a mythical doo wop record that was rerecorded (the masters were lost) and pressed up and passed off a repress of the original...
the mob was also bootlegging records by at least the late 60's and the emergence of the youth oriented FM/LP market (they'd pay off guys to run the presses at night or find a small pressing plant that'd look the other way... you can find these records sometimes, they look about 90% like a real release, but something is a little off...)
in terms of live bootlegs, they begin with Bob Dylan and Rolling Stones stuff ("liver than you'll ever be", taped on their 69 tour may be the best live rock record i own) in the late 60's... they had plain white covers with just a stamp on 'em... Clinton Heyden's "bootleg" is a very cool telling of those days and up...
the 70's is when reissues/bootlegs of old stuff really took off... there are tons of bootlegs of old rockabilly and r&b 45's that date from the 70's, i have one of one of the first motown 45's ("whole lotta woman" by the contours)... if you go into 45 only shops run by cigar smoking old man who listen to talk radio all day, they will def STILL have a pile of stock of that type of stuff that they bought in the 70's... there are also jenky versions of old Little Richard stuff on the TRIP label which feature lame takes from the 70's of rocking 50's stuff... these are from the early 70's, when "American Graffiti" brought back nostalgia from the 50's...
on the official side of things, the mid 70's is when Shelby Singleton reissued all the classic Sun country and rockabilly on a revived version of the Sun label... King records was also revived to release their 50's/60's material from people like Hank Ballard and the Midnighters in a similar fashion in 1976... it's also when RCA reissued the early Elvis Sun Sessions... i am attributing 76 as the magic year to a combination of a burgeoning record collector underground and another nostalgia boom, due to Fonzey and "Happy Days"
tho, it might just have been something in the air, as in the UK, Charley begin not as a r&b label, but as a rockabilly label, even hitting the charts with Hank Mizell's tune "jungle rock" in 1976... in fact, if you look at the UK charts right before the dawn of punk, a lot of the charts was either greatest hits of current artists or cheapo reissues of 50's and 60's stuff...
now for the garage/psych part of the story:
Lenny Kaye's Nuggets comp, released in 1972, and collecting garage psych records from 66-68, was, i think, the first rock record to collect old records with a real intellectual purpose (as opposed to Golden Oldies type comps). after the death of psych, and eevn proto punk (bands like the Stooges, MC5, and VU were either gone or on their way out) and before the rise of punk, there was a void in hard, catchy 2 minute 30 second songs (remember that Glam Rock made no impact in the US)... i have seen Lenny Kaye out at around NYC and i would be curious to ask him why/how Electra issued it and what gave him the idea...
with the dawn of pub rock and punk, Nuggets was reissued by Sire in 1976... at that point, a real underground of garage/psych collectors had started to develop thru fanzines and record trading... people like Jeff "monoman" connelly, the singer of DMZ, a late 70's boston band whose first record from the 1976 contains covers by both the Sonics and the Wailers... he became "famous' w/ the Lyres, but really started out as a record collector...
at this point, you have the magic recipe for bootlegging: enough people who are sweating records to pay hundreds for 'em (and lots of casual fans turned on by punk bands covering old garage songs), yet not enough to merit a mainstream release... also, consider that most garage/psych 45's came out on a small labels that had long since gone out of business by the late 70's... so, proper reissues would be exceedingly difficult...
so, pebbles sprung up in the late 70's to fill the gap... gradually Rhino records began reissuing their own Nuggets series, in the early 80's... (they started as a novelty label, but began doing reissues by the late 70's)
from there on reissue culture explodes to the point that the major labels get in on the act and reissue tons of their 60's catalogs...
with the exception of Charley, i don't know too much about UK reissue culture, except to guess that alot of it comes out of the market stall records shops of the pub rock days that specialized in 50's and 60's music...