I've spent a lot of time in the last few years thinking about which edition of D&D is the best for me. I've got some real fondness for Basic D&D, AD&D 1E, OD&D, and I even think that if I was going to run the original Ravenloft: Realm of Terror boxed set I'd be willing to go with 2E just because that set is so brilliant(although I wouldn't pick 2E under many other circumstances). So. . .which edition (or retroclone) is the one I'd prefer? The answer is: there's good and bad with all of the above editions. There is no one ideal choice (although Moldvay comes pretty damn close in my book) which, I suppose, is WHY we all keep re-engaging with these rules.
I though I'd sort of found my answer in OD&D several years ago when I first stumbled onto Philotomy's OD&D musings (which you can find at http://www.philotomy.com/ ) . Initially, I was pretty fundmentalist. I thought: "Okay, just the three brown books from the original OD&D set. Who needs the Thief and screw variable weapon damage! We are going to go as old school as you can get!" Well almost. . .I didn't decide to play some crazy Blackmoor-styled Chainmail variant (although reading about that stuff is inspiring). Problem is that I almost never got to play OD&D, and when I did play it became clear that some of the elements of later editions were more valauble than I'd first believed. For example: I wanted more classes!
Which then led me to crack open my AD&D 1E Player's Handbook, and The Dungeon Master's Guide. The rules were both cumbersome and obscure in places, and in others as clear and as simple as daylight. My time looking at OD&D was very helpful, because for the first time I saw how AD&D had both retained and tried to move away from the previous ruleset. Instead of being clearer, AD&D was just obscure in different ways. I needed help, so I looked at OSRIC. I read posts online at various forums about AD&D. I studied, and I thought. In the end, I created a house rules document (which I posted here a few months ago) that took out all the stuff I didn't want, so my AD&D ended up looking more like OD&D. That was the hewing back AD&D approach, but it occured to me that there was another route to go as well.
What about OD&D with the supplements? That's when I started looking at Swords & Wizardry as an option. The PDF was free afterall, right? After poking around a bit, I found the wonderful S&W Companion at http://swcompanion.wikidot.com/ . The supplement at the S&W Companion site called White Box Heroes was pretty much exactly what I'd been looking for. So earlier this summer I ordered both S&W White Box and White Box Heroes from Lulu (along with the excellent S&W Monster Book).
I'm in the process of prepping a session for this Thursday with my gaming group. We decided that I was going to run a one shot of old school D&D for two of my players who are pretty much new to roleplaying. So what was I going to run them in? Moldvay? Holmes? AD&D? Nope. After almost deciding on Moldvay, I decided that using S&W White Box with the White Box Heroes book was just about perfect for new players. I revised an old OD&D character sheet I made, and I even created a house rules document and some reference sheets that are pretty spiffy.
I'm curious to see how OD&D/S&W plays with a few more options. I'll definitely post about it here afterwards.
In the end, I'm like a lot of folks who seem to be looking for something with the core simplicity of OD&D/Basic D&D with many of AD&D's options. James Maliszewski at Grognardia has called this D&D 0.75. The link to his post is here.