Could use some insight here

I'm looking to get "back" into D&D typing gaming after about 35 yrs away but I have ZERO clue about the different genres and systems etc. Can someone recommend a good starting point or group? I'm in the NYC area and can probably play monthly to start.

Put it simply. DnD 3e/3.5 Most crunchy (meaning rules heavy), Hard to get into, But most options out of all wotc DnD. DnD 4e MMORPG style DnD DnD 5e Rules light, Easy to get into, But lacks Options (when I mean lacks options its basically cookie cutter kind of deal)

Welcome back! I returned after almost as many years away from the game.  Stopped just when 2E started coming out having played through basic and AD&D (1E).  ShadowDragon has the 3/3.5 and 4 described pretty well.  I will disagree with the 5e analysis.  It is rules light, which gives room for a lot of customization for those who like to keep things light or make it heavy and gritty.  WOTC even included optional rules to guide people along those lines. I found it really easy to pick up and start DMing again. 

I might have a slightly additive/altered POV on it a little different than Shadowdragon I would just up front, personally recommend 5e. It being the most current version in use has certain advantages in terms of finding others to play with. I come from ADnD and 2nd as my introduction and first longer term use of, so my perspective includes those lenses. 3e/3.5 = this is a miniatures board game rule set more than a story telling RP rule set. i.e. spell descriptions include player (not charater in lore) facing mechanics that assume you are using minis on a grid board. 4e, yeah kinda an oddity by my eye, this is trying to make a table top MMORPG of DnD. More streamlined in the board game mechanics rules than 3, but by my eye, still more in the deep weeds of minis board game rules than more open ended RP flavor lore as rules. As far as i gather this is kind of the cult version where some really like it, but by and large it did not receive wide spread love. 5e = getting back to a more story drive RP game, rules allow for play out on grids, but also make it easy enough to just whiteboard scribble out maps on the fly as you go and use not scaled dots/markers whatever works. This is a fairly streamlined version of DnD, while still by my eye being a rules complicated RP game relative to others that have been developed over the years.  I like 5e a lot, feels like a more rationally put together ADnD/2nd edition(2e) that plays a lot like older school DnD, but got a lot better about the roll or die junk. My one beef on 5e is probably that every character is Wolvorine self healing back to max if they can get a normal full nights sleep in. If you take 49 out of 50 HP, one full nights sleep is back to 50 hp. So as GM you have to wind up taking control of simply not allowing players to get in long rests too often, before you force them to face more danger, or there feels to be too little real danger in 5e.

5e is your basic game. If you want to play in easy mode all the time, that's the way to go.

@Onginme and @Social Yeti I tried to give all systems at least 1 good and 1 bad sometimes more to give a good view. My descriptions may not of been best. But I was not trying to play one system over another. I apologize if it seemed that way. I just wanted to show what I considered good and bad from all of them.

You have all simultaneously given me a lot to digest and somewhat confused me...lol and I appreciate it greatly.

Hey Mike, Don't forget, you can find plenty of old-school games (1e, 2e, BECMI) currently looking for players, and it can actually be easier to get in, as they're not flooded with 5e applicants. If you want to ease your way back into playing, you can always opt to start back in with an edition that you know. They still remain perfectly functional rulesets, and I for one actually prefer them because they have more of the gritty medieval feel I like, where the later editions feel to me like a mash-up of medieval and superhero genres. To each their own, of course.

check into "the OSR" (movement, style, genre), stands for Old School.  This can be a lot of different game titles, that can be found in Roll20, for example OD&D, AD&D, 2nd Edition, Old School Essentials, Basic Fantasy, Labyrinth Lord, Swords & Wizardry, Castles & Crusades, Dungeon Crawl Classics, BECMI (Basic, Expert D&D).  All of those types of games can be fun, playable, accessible, affordable, familiar, and they are being played in roll20.