Help Me Complete Holes

[Drakul]

I already have a sizable collection (see here) but I'd like to complete the stuff I'm lacking. Some things I'm already planning on grabbing such as the Red Robins, Nightwing the Target, ... of the Owls, Death in the Family and the Murderer? / Fugitive reprint but I'd like advice on the rest .

Here's the list of what I'm missing and debating buying (mostly stuff between OYL and flashpoint), I'd like to know which you recommend first as essential for continuity (i.e you should really read X before getting into Y because you'll miss a bunch) and second as simply a good read (i.e Arkham Asylum is not really in continuity but it's awesome so you should read it.). Of course let me know if something sucks so I can skip it without remorse to avoid another Fortunate Son.

Year Two
Riddler Prestige
Two-Face Prestige
Turning Points
False Faces
Batman/Nightwing Bloodborne
Poison Ivy Cast Shadows
Hush Returns
Robin To Kill a Bird ; Days of Fire and Madness ; Teenage Wasteland ; Big Leagues ; Violent Tendencies ; Search for a Hero
Nightwing Mobbed Up ; Renegade ; Brothers in Blood ; Love and War ; Lost Year ; Freefall ; Great Leap
Face the Face
Catwoman The Replacements ; it's Only a Movie ; Dies ; Crime Pays ; Long Road Home
Birds of Prey Club Kids ; Metropolis or Dust ; Platinum Flats ; Oracle Cure ; End Run
Gotham Underground
Azrael Death's Dark Knight ; Angel in the Dark
gotham Shall Be Judged
B&R Dark Knight, White Knight
Batman Incoporated
Gates of Gotham

Once I grab what I need form the above I should have a pretty complete pre-Flashpoint collection.

[GrandKaiser]

Year Two - The Reaper is an incredible anti hero/villain, everything else about that story is crap
Riddler Prestige - What is that? -
Two-Face Prestige - What is that?
Turning Points - Not really necessary unless you plan on reading Officer Down, Turning Points serves as a prologue to that storyline
False Faces - BKV is great but the volume I have barely features any Batman. It's basically just a compilation with a pointless Wonder Woman story.
Batman/Nightwing Bloodborne - This was just a one shot, right? I enjoyed it. It has a cool noir style with great art + colors. Story is okay.
Poison Ivy Cast Shadows - VERY underrated. Definitely recommend picking this up if you like Poison Ivy. Ann Nocenti is great.
Hush Returns - This book is horrible. Every single character is written poorly including Hush who was a stupid character to begin with only spends time going after the Joker
Robin To Kill a Bird ; Days of Fire and Madness ; Teenage Wasteland ; Big Leagues ; Violent Tendencies ; Search for a Hero - HIGHLY recommend this book and the sequel series Red Robin.
Nightwing Mobbed Up ; Renegade ; Brothers in Blood ; Love and War ; Lost Year ; Freefall ; Great Leap - Worth checking out, the last few issues aren't great though.
Face the Face - Great mystery story, and it gets very poignant toward the end. It also sets up Batman & Son pretty nicely.
Catwoman The Replacements ; it's Only a Movie ; Dies ; Crime Pays ; Long Road Home - Love this whole series but it's not essential
Birds of Prey Club Kids ; Metropolis or Dust ; Platinum Flats ; Oracle Cure ; End Run - Club Kids is the eighth volume of that series and the rest go on after that. I recommend starting the series with the 7 previous volumes.
Gotham Underground - Not essential. It's great if you're into Batman's rogues gallery but the story tackles an array of interlocking plots and characters that make it hard to follow.
Azrael Death's Dark Knight ; Angel in the Dark - First volume, Death's Dark Knight, is not bad. Kinda spooky and cool. I never read it after that but I heard it dropped in quality.
gotham Shall Be Judged - SO boring. Like, really boring. The story introduces a promising team up--but fails to deliver anything interesting beyond that. Not a fan.
B&R Dark Knight, White Knight - I suggest you read the entire Grant Morrison B&R run. It's meant to be a sendoff for Dick & Damian, and I don't think it'll connect with you if you haven't read their series. It's divided into three chapters and Tomasi's part is the best IMO.
Batman Incoporated - The first series is alright. It takes a while for things to really get going. The second series is AWESOME. So much fun.
Gates of Gotham - Definitely the best DickBats story after the Black Mirror. Reading it actually makes me miss Dick Grayson as Batman. It's wonderful.

[Drakul]

I'll check your answers in detail later cause I'm heading out but FYI I only listed stuff I don't have. If you click the link in the OP you'll see I already have all the Dixon BoP trades and the previous 3 B&R.

[nepenthes]

Incorporated crazy that you haven't ready these yet
Azrael: Deaths Dark Knight great arc and covers much of the timeline gap in Morrisons run
Gates of Gotham very decent Grayson era Batfamily arc: last hurrah of the pre New 52 era
Search for a Hero vintage Tim Drake will help you appreciate the character and era he came from; can take or leave the rest but this is the intro
Nightwing, Catwoman grab the first volumes to see if it's your thing; they're not hugely important continuity-wise

The rest I wouldn't bother with, though a lot of old school Nightwing fans might disagree

[Drakul]

Incorporated crazy that you haven't ready these yet

Yeah about that... I'm reading Batman in order so I'm behind. Like I'm almost at NML :P
When you say "grab the first volumes" you mean after 52-OYL later I assume?

Thank you both for the reco.
So far I'm getting across the board recommendations for Robin, Incorporated (which seems essential anyway) and Gates of Gotham as well as some more muted but still leaning towards a grab for Turning Point, Poison Ivy and possibly Azrael.
For Nightwing I'll probably grab the 2 Grayson trades and maybe the Tomasi ones but skip the rest.

Still on the fence for Year Two, Bloodborne, Catwoman and Dark Knight/White Knight.

I'll skip False Faces, Riddler prestige and two-face prestige, Hush Returns (everyone says it sucks but can i skip the story or is it still important?) and Gotham Shall be Judged.