Okay, so there has been a lot of discussion lately on blogs and G+ things I follow on "What is the OSR?" As I see it the OSR has two communities and they overlap some (how much is open to debate). One community is what I'll call The Grognards. These are people who started playing D&D back in the AD&D 1st Edition era or earlier and still play an early edition. They love the original rules, are super-nostalgic about campaigns they were in, the early modules they played, etc. They have reams of house rules, might have miniatures, but never used a battle mat. The other community is The Hipsters. This group loves the early editions for their quaint simplicity and the default requirement that you must house-rule a lot because of their primitiveness. This is generally younger DIY community wants to make new stuff, such as Red and Pleasant Land, Lamentations of the Flame Princess, Old School Hack, White Star, etc. using the early editions as a jumping-off point.
Where do I stand? Well as I've mentioned before I played the original D&D rules in the white box back around 1978 and thought they were atrocious. After a couple sessions, including my first cleric and a dangerous raft trip down a river, it was obvious to me D&D would never catch on. A couple years later, in college, I played a monk in a really fun AD&D 1E campaign run by my friend George. At that point I was still appalled by the cludgy, primitive, random rules but I could see the fun aspect of all the random tables and thought the classes, spells, and monsters were way more interesting than the ones in the rather stodgy Chivalry & Sorcery rules I was using. Today I still wouldn't play anything pre AD&D 1E (or Chivalry & Sorcery for that matter). I would definitely consider AD&D again (my nostalgia game) or a clone, such as Swords & Wizardry or Adventurer, Conqueror, King System (ACKS). The later 3.5E and Pathfinder rules (I sort of skipped AD&D 2E) are very attractive but the massive crunch level and rules bloat is tough to keep up with. I missed the 4E era but admire the clean design approach. I've played 5E a little and think that it's probably (currently) the best balance between the early simplicity and later "modern" rules design concepts. And of course I love Old School Hack and my own Neo School Hack of it.