At Sundazed.com, you can purchase a Great Society CD called Born To Be Burned. It is great! I highly recommend it. It has three versions of Free Advice.
As far as the questions that the original poster put up (Who, When, Why, How, etc.?), here is what the liner notes of the CD says:
Remaining true to their modal muse, the band returned to the studio in December (1965), this time under the eye of Autumn's house producer, Sly Stone, to cut Darby's two noisy masterworks as their debut single: "Someone to Love" and "Free Advice." Both sides, however, required multiple takes before they were captured. "We did one version (of "Free Advice") that was wonderful early on, and the engineer said, "Oh, I didn't get it. Can you do it again? An that's when we went into that hundred takes (actually 53) mode. It was such a letdown that we just lost it." Eventually surfacing on Autumn subsidiary Northbeach, the single did nothing nationally and was barely available even locally.
On the inside of the Jefferson Airplane Box Set Booklet it says this about Free Advice:
6. Free Advice
Artist: Great Society
Taken From: Morthbeach Single # 1001. Courtesy of Rhino Records, Inc.
Producer: Sylvester Stewart
Recording Date: December 1965 (Golden Gate Studios, San Francisco, CA)
Personnel: Grace Slick, Vocals; Darby Slick, Lead Guitar; David Minor, Vocals, Rhythm Guitar; Bard DuPont, Bass; Jerry Slick, Drums; Billy Preston, Drum Overdubs.
Wow, how awesome was it to have the great Billy Preston play on your first single! Lucky, I guess.
~Remember What the Dormouse Says, Feed Your Head! Feed Your Head!~