This is why I think Crescent is so underrated. You for example have heard Ascension, Interstellar Space(!) and One Down, One Up, but not Crescent. Pretty much everyone who I know who has heard Crescent would name it as one of their favorite Coltrane records. Based on that I'm quite confident you're in for a treat. It certainly won't be your gateway into free jazz, but it sure is one fine record. I recently got the Original Recordings Group limited edition vinyl and it sounds truly glorious.
I think I'm blessed when it comes to free jazz, because I simply liked both of the first two albums I heard in the genre, which were Ornette Coleman's Free Jazz and Coltrane's Ascension. It took me years to learn to appreciate Ascension on more than a superficial level, but just the sheer amount of energy on that record excited, intrigued and shocked me all at the same time when I first heard it. Free Jazz I just found instantly likeable from the get-go. I've never really witnessed a person I know learn to embrace free jazz. Everyone I know either loves it or doesn't. I was shocked when a cousin of mine who currently studies music technology and composition at a university in London recently recommend a group called Supersilent to me. All of their music is very avant-garde free improvisation much akin to free jazz or what most would even call free jazz. Only a couple years ago I remember mentioning him something about how much I enjoyed Keith Jarrett's solo piano improvisations and he just made a short comment about not liking improvisation or something. I guess he's made quite a leap at some point, likely because someone recommended something to him. We've known each other since childhood and share similar tastes in music, but sadly I wasn't there to witness his transition to appreciate free improvisation.
What I'm trying to say is that I have no idea how one who doesn't just naturally enjoy free jazz learns to appreciate it, apart from putting effort into liking it. Music appreciation and taste are not something I think we have from birth. It is something we acquire through time, experiences and exposure. When I was a child I didn't like music, hated it. I couldn't fathom why anyone would listen to music. I'd never heard anything I liked and only when I was around 14 or 15 I made my first attempt to buy a couple of CDs and try to find out what people though was so great about music. The musical education I got at school was rubbish and only further discouraged me from wanting to appreciate music. Those first albums I bought were all awful and it was only a few years later that I discovered some music that I liked and channels through which I could discover new good music. That story is too long to retell here, but nowadays music is the biggest thing in my life and I couldn't imagine living without it. For the past decade I've probably bought somewhere in the vicinity of two to three hundred albums per year on average and I only continue to discover new sources for music. Every time I embrace a new genre, it takes me months to learn to appreciate it. Two years ago I wouldn't have imagined I'd ever find myself listening to trance or house because my first experiences with EDM in the early 2000s were very negative. Then I came across a couple of artists whose work I adored and spent the next six months exploring the vast sea of genres and artists out there. Now EDM is one of the genres I listen to most often on a daily basis. In the end I think it all comes down to how much effort one is willing to put in. There is something to like about virtually any genre, I feel.
Edit: It helps when you find that perfect personal entry point into a genre.
Thanks for the tip.
I'll have to track down "Crescent" on ORG LP.
I'm a big fan of vinyl.