D&D - - - - AD&D / Basic,etc. - - - - 2nd Edition - - - - 3rd / 3.5 - - - - 4e / Pathfinder,etc. - - - - 5e - - - - OD&D (tbd)
Added Pathfinder as it really was similar to 3.5 D&D when 4e happened

Started playing with Basic D&D along with 2nd Edition shortly after, then ended with 3rd/3.5 as afterwards other things in life happened or only played other rule sets.

D&D I played the first time on the day before Bob Bledsaw's funeral and enjoyed it.
AD&D I am sure is what my brother ran me through or I watched him DM his friends when I was younger.
Red box (Basic set) was the first item he bought me that opened up the flood gates of fun and creativity.
Ravenloft for 2ed was mine, not the novels or materials for other worlds during that time that I borrowed, I bought it, loved it and continue to buy anything with Ravenloft on it to this day.
3/3.5 being the open license for countless companies boils down for me to White Wolf's S&S line providing a lot of things during that time. Other companies/settings, etc of course were great and some I continue to support but S&S was the beginning.
4e I bought the 3 core books, very little else. Nothing memorable.
Pathfinder continued after Dungeon Magazine with great adventures. The goblins made this setting for me.
5e got me to buy more then just the core books and of course other companies continue to support it. Have like some of the settings as a result.
One D&D time will tell - I will get the core books.

ShaneG.

I started playing Holmes basic in 1977, switched to AD&D as the hardcovers were published. I never played 2e/3e/3.5e/4e. I taught my children 1e, but then also 5e because it occurred to me that's what their friends would be playing.

AD&D (hardbacks and early modules). Returned to that in recent years, though also using (i.e. converting) 5th Edition adventures, which I think are really high quality.

What did you start playing, end with, and like from each D&D

I began playing with the Basic and Expert sets many years ago.  I liked the simplicity of these editions, but the complexity could be limitless, if desired.

For many years I've mostly been a DM, but I occasionally get to play, usually at conventions or in one-night or weekend adventures.  I've DM'd and played all editions, but the primary edition has been 1st, with some 2nd interwoven into it.

When not using unique material, I'll use just about every edition, the least used is 4th edition.  I also incorporate material from third-party systems.  Some of those systems are: Arduin, Castles & Crusades, Dangerous Journeys, DCC, Lejendary Adventure, OSRIC, and Talislanta, among others.  I've also played and DM'd Sci Fi, Historical, Horror, and other genres.

As far as what I'll end with, we'll see.

I do like a lot of the 5th edition material and mechanics.  It's also one of the easiest editions to incorporate into a 1st/2nd edition campaign.

I guess which set we started with would correlate with our age. Like many here, I started with Basic and Expert rules. I purchased Companion, Master and Immortal sets back in the day. I think I played with the Companion set a bit then moved onto 2nd edition. The times I have been able to play throughout my life I have stuck to first and second edition. My children played 5th edition at school, but their descriptions of their gaming sessions all sounded a bit strange to me. The times I managed to run games for them I stuck to 1st edition. Keep on the Borderlands and Isle of Dread bring back the fondest memories, oh and Sinister Secret of Saltmarsh  - had fun DM'ing that series for my boys years after I played them.  

First two 2-person sessions were Holmes. First group plays were Moldvay for two kind of short campaigns.

Joined D&D club a few weeks later in '82, but couldn't make regular sessions (Band lol) so jumping around alot on what I was playing when I did.

The club version of D&D was a streamlined mix of 0E & Runequest as I understood it at the time. It looked and played great from what I remember.

My home campaign was City State and RoleAids stuff mostly. Friends I played with the most liked Mentzer the best.

It's hard to think of it as "just" 1st Edition when it seemed to change so much over time as things were released. Some of those Dragon and WD articles hit hard too

Never played 2nd, own and read the 2E PH though. For an opinion I'd guess after Unearthed Arcana, tsr was going to have to do something with the Kraken they unleashed. It seemed to clean up some things, but at the time all I ever read was the PH.

The last game I played was 1.5++ and pretty gonzo, about a 3-4 month campaign around 1990.

The success of 3rd Edition got me interested in collecting D&D but still haven't played it. Read some modules and free OSR stuff, seemed overly complicated (to me) but I liked some of the changes. I've never read any of the core books nor watched anyone play so I limited on opinion.

Read a 4th ed module once and thought it was for children. That's all the effort I've given to it - sorry.

I've read nothing for 5th ed. Watched a little CR (about 15 minutes). I have listened to or watched some people talk about 5th ed, most of them bore the shit out of me or are pretty annoying. I guess an exception to that would be people like Ginny D. Pretty basic info but has a nice voice, something to listen to that's pleasant around nap time.
For an opinion though, things I didn't like in 3rd are still present for what I know. Things that have changed I guess are for the better. When I'm in the dice groups with young players and they talk about the game, it reminds me alot of some of the people I really liked playing Basic/1E with. The people that spent less time talking about rules or more time playing. I'm kind of simple like that.

6th Ed - I think they're stuck with doing a major online component, they won't get the young masses without it anymore (if that matters, I think it does). How that goes will determine the outcome.
Pretty pitiful start on the Product Name, guess keep your fingers crossed.

I'm quite young (being merely ~40....)

Still, hard to remember but started 2nd ed sometime early 90's. My salient memory of the first campagin I played in was attempting to charge a party member for healing in the dungeon. I was about 8-9 I believe.

15 years later with most of the same group every weekend, I never lived that down.

Subsequently played 3rd/3.5 and also 0/1st later on.

Played a fair bit of the Call of Cthulhu rules from around year 2000 - though i have no idea how they were before or since.

I started in late 74 or early 75 at The Little Soldier Shop in Wheaton, Maryland.  I went from OD & D straight to AD&D.  Never played Basic or any of the BECMI versions.  I quit in 1982 and then picked up with 5E more recently when my son got interested.