Over the years, moving from vinyl thru cassettes to CDs, the ones I play most are:
Gordon Lightfoot -- every album I can find including some that other people put together as "greatest hits" disks.
Ian & Sylvia -- ALL the Vanguard releases
Ian Tyson (solo after his move to Cowboy/Western) -- "I Outgrew the Wagon & Other Cowboy Culture Classics" and "18 Inches of Rain"
Patrick Sky -- Original album title "Patrick Sky" and "Gentle Harvest of Clang"

Less frequent play goes to another music genre: All the Creedence Clearwater albums, Queen's "Night at the Opera", and a variety of other artists.