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On the whole I found 5 (ps4 so far, copy of 5 switch might be coming tomorrow though, or tuesday if not. Super excite!) to be much better than 4, but I'll go through the points:

> Which has the most content including DLC?

Unsure exactly, as I have yet to get 4 on the Vita and dislike buying the DLC for the console versions. It's worth noting that 5 Complete (as well as all of the handheld versions of the games, barring 2 kind of) comes with the DLC packaged in where if you were to get the console version of 4 it doesn't include any of it. It's not particularly cheap to buy either (although if you can get the base game for ~$10 that's pretty much balanced out lol). I believe the base campaign is a little longer in 5 than 4. Post games will tend to be equalish length.

> Is it worth playing D4 just for the story?

This I feel isn't exclusive to just 4, even though 5 is the best mechanically speaking, I would argue that if you end up enjoying the series it would be worth playing any/all of them for their stories. especially for as cheap as you can get them now xD One thing I would look into since you have a PS3 is: This collection. A lot of game for the cost xD That said, I wouldn't delve into the post game of the older entries. Things have gotten much more manageable as time has gone on, like ease of grinding and such.

> If I play D4, will I still be interested in D5, or is it alot of the same?

I would think so. As a fan of the series I'm always looking forward to the next entries (I played them in the order 1 -> 3 -> 4 -> 2 -> 5). This ties back into the fact that they all have fun stories and so are very different games in that regard. 4 and 5 specifically is kind of tough because the stories/character motivations are kind of similar-ish, but they're definitely different enough to be unique.

> Did they remove any features/gameplay mechanics that were present in D4, and not in D5?

Not that I can think of. There were game-specific features taken out of 2 going into 3, and 3 going into 4. I suppose technically 5 uses the "old style" weapon mastery system, where characters have profficiencies for different weapons, and you can equip them with anything but having a better proficiency levels it up faster which leads to new skills faster and more damage faster. In 3/4 they changed it to a system where each char just had a set of weapons they could use/learn skills in. You could equip them with other weapons, but they couldn't use the skills from them. You /could/ fix that by utilizing various systems but it was somewhat less ideal that the current one where anyone can use anything easily. So the good one's back~

> Should I even start as a newb with D4? Other title suggestions? I own a PC(Steam)/PS3/Switch, so I have access to all the Disgaea titles.

I think you're fine starting anywhere anyways. I would recommend Disgaea 5 for the best gameplay experience, but I also don't think it has one of the better stories the series has to offer. Really it depends on how jarring you find going backwards, gameplay-wise. If that's not a big deal to you, I'd recommend 5 to get introduced to the series, then play other ones that seem interesting to you. But if you can only go forwards, definitely at least play disgaea 1 on PC or PS3 (I think you can get in PS3, maybe not). It's definitely a classic and should be experienced. Then you could branch out to whichever games you liked. 3's my personal fave, cast/story wise, school theme. 2 has a pretty good story, but some weaker side characters. 4 is something of a political comedy at first and has some of the more humorous overall casts in the series. 5 I like the main chars a lot, but overall narrative not as much. D1 also has a sequel, DD2 (it's in that collection I linked) that should probably be played only after D1. I've not played it yet so I don't know how vital playing D1 first is, but it's a direct sequel so... yeah xD

First of all: Welcome to the Netherworld!

If you're wanting to dig into the series, I'd recommend starting at the beginning. The primary reason for this is that the game mechanics have evolved over the years, and if you start with the most recent games you may find the older ones more frustrating. The original Disgaea was a PS2 game (Hour of Darkness) that also has a PSP release (Afternoon of Darkness), as well as DS. In February it will be releasing on Steam for PC for the first time as well!

If you don't mind skipping a few titles, then starting with 3 should be fine. The Vita versions can be purchased directly from NIS America's webstore, and perhaps a few select online retailers. (Example, here's Amazon US's page: http://amzn.com/B006FRMVIQ )

Be aware that Disgaea is built on the foundation of silliness, massive numbers, and grinding. It is FAR more light-hearted than Final Fantasy Tactics. As long as you embrace this from the get-go, you'll have a wonderful time! If you have any additional questions, feel free to ask, I'll respond when available. You can also PM me.

Cheers, and hope you enjoy the shenanigans!

I'm assuming you're a US citizen, but... dood,

• Playstation TV: https://www.amazon.com/PlayStation-TV/dp/B00KVMHSUM/ref=sr_1_1?ie=UTF8&qid=1487863174&sr=8-1&keywords=playstation+tv
  
• Disgaea 3 Vita: https://www.amazon.com/Disgaea-3-Absence-Detention-PlayStation-Vita/dp/B006FRMVIQ/ref=sr_1_1?ie=UTF8&qid=1487863200&sr=8-1&keywords=disgaea+3+vita (there's a patch that makes it PSTV compatible)
  
• Disgaea 4 Vita: https://www.amazon.com/Disgaea-4-Promise-Revisited-PlayStation-Vita/dp/B00M9EZMN0/ref=sr_1_2?ie=UTF8&qid=1487863200&sr=8-2&keywords=disgaea+4+vita
  
  I know it's extra expense, but $110 (plus any applicable sales tax for your state) ain't half bad.
  
  PSTV works with PS3+4 controllers afaict (it works with mine but mine's fully patched!), so... you should be good to go.
  
  Other than that... Disgaea 3 was a decent game, Disgaea 4 is FAR superior to it. Get D4 before / instead of D3 if budget's a concern.
  
  That and you can pick up Disgaea 1 Afternoon of Darkness PSP version and Disgaea 2 PSP for it too... :p guess what I've got on my Vita? :D
  
  Disgaea 5 beats both of them on convenience of the game's systems etc. It's really well done. So get Disgaea 5 to go with your new PS4, and then think about the Vita versions of the prior games, maybe :)
  
  EDIT: $31 for the Triple Play: https://www.amazon.com/Disgaea-Triple-Play-Collection-PlayStation/dp/B011L4CFB0/ref=sr_1_1?ie=UTF8&qid=1487863466&sr=8-1&keywords=disgaea+collection - so a cheap PS3 might be a good way to go if you can get that!
  
  PS3 is also a blu-ray player so if you're the kind who needs a blu-ray player for a second room, ... there's a convenient excuse for you :D

>I don't have a console or a portable system, but I'd probably buy one for a more refined version of this, are the mobile ones good?

You probably get the most gameplay for your money if you get a used PS3 for ~100$/€ and the Disgaea Triple Pack (Disgaea 3+5+d2d) for ~35$/€.
Though, with a bit of luck, it may very well be possible that the other Disgaea games will also be ported to the PC.

Uh, have you seen This yet??? If you have and still only want 1 I'd suggest getting DD2. It's the most streamlined and fun. It features the original cast and I feel has more content as well.

I would love to, but it uses a charging dock...
(http://www.amazon.com/Nyko-Charge-Base-360-Xbox/dp/B00273Z9WM)

Do you need a digital copy?

https://www.amazon.com/dp/B00RUZPKYY/ref=cm_sw_r_cp_awdb_NmgtzbQXSXXDA

Way cheaper on Amazon.

@rifledemon - Amazon has the guide for preorder $26.13: http://www.amazon.com/Disgaea-D2-Brighter-Darkness-Official/dp/0804162131/ref=sr_1_2?ie=UTF8&qid=1376460279&sr=8-2&keywords=disgaea+d2

I only found this:
https://www.amazon.com/Disgaea-Triple-Play-Collection-PlayStation-3/dp/B011L4CFB0
Didn't find a double pack. Also the above doesn't include any DLC.

Basically it was an incomplete guide of terrible quality, and taught me never to buy anything that bradygames puts out again. Typos, inaccurate information, duplicate pages, very short. The content that was there included virtually none of the cool tables doublejump guides had, it didn't even really provide a sufficient walkthrough. The gamefaqs that you can get now are 1000x better. Looked like it was put together by an intern and nobody got around to editing it. Just terrible.

Check out the amazon reviews. Selling this thing to people was just embarassing, and all parties involved should be completely ashamed of themselves for letting it happen.