For me it would be pretty interesting. First off, as great as the Women's roster is right now (Perhaps the best it's ever been) I cannot see them having enough for a thirty woman rumble. However, you can do 15 easily. 
You are only allowed two surprise entries

Now let's say that Becky Lynch and Charlotte keep their belts all the way to the Rumble: 

Here would be my entry order: 

1. Naomi 
2. Ember Moon (Literally just getting the longer entrances out of the way)
3. Bayley (Give her the Underdog treatment)
4. Alicia Fox 
5. Nikki Bella
6. Maryse Oulette (Surprise entrant)
7. Carmella 
8. Alexxa Bliss
9. Emmalina....? (Although she should ditch it an go back to being Evil Emma)
10. Nia Jax
11. Blue Pants (Surprise Entrant)
12. Natalya
13. Dana Brooke 
14. Sasha Banks


And just as it looks like Sasha Banks or Dana Brooke or Nia Jax is about to win.... Out comes.... 
15. Asuka (Making her main roster debut)

Now here are some notable spots here; 
By this time; Ember Moon will have beaten Asuka for the NXT Championship, so instantly the first person Asuka takes out will be Ember Moon. 
Blue Pants will hold the Women's record for quickest elimination (By Nia Jax of course) 
And the Final four would be; 

Nia Jax, Bayley, Alexxa Bliss and Asuka 

Bayley, Alexxa and Asuka all recognize Nia Jax as the biggest threat so they all take her out. 
Just as that happens, Charlotte comes out and literally screws out Bayley of the match, only for Dana Brooke to come to her aid and take the fight outwards. 
Meanwhile, Alexxa and Asuka are your final two. After a good give minutes though; Asuka wins with a hip strike taking Alexxa off the top. 

It sets up not one but two matches for WM actually. For one, you get; 

Becky Lynch (c) vs Asuka for the SD women's title

But you can also use it as build up for; 

Charlotte (c) vs Bayley vs Dana Brooke

Have Asuka win.

Alexa Bliss wins as the SD Women's Champ already, then wins the Raw Women's Title at Mania becoming the Undisputed Women's Champion! Because fuck every other bitch besides Alexa <3

Nastradamus wrote:

Alexa Bliss wins as the SD Women's Champ already, then wins the Raw Women's Title at Mania becoming the Undisputed Women's Champion! Because fuck every other bitch besides Alexa <3

Step aside and let a TRUE legends some through.

The order of entrants

1. Sasha Banks
2. Bayley
3. Dana Brook
4. Eva Marie
5. Naomi
6. Nikki Bella
7. Emmalina
8. Natalya
9. Nia Jax
10. Carmella
11. Trish Stratus (surprise Entrant)
12. Summer Rae
13. Mickie James (surprise entrant)
14. Paige
15. Alexa Bliss

The Booking: Sasha enters at the babyface number one spot after being forced there by Foley/Steph after losing to Charlotte and getting handed a title shot time after time.  She comes in confident until Bayley's music hits.  They immediately go whole hog at one another, let the first few minutes of the match prior to the 3rd entrant be all about them showcasing how well they know one another and how well they work.  Dana Brook comes out and tries to play rain cloud on the moment, immediately sideswiping Bayley with a clothesline.  With the old "Nobody can beat up my brother but me" mentality, Sasha hits the Bankrupt on Dana.  Dana teeter totters off of Sasha's knees right into a waiting Bayley's arms.  Dana gets the Bayley-to Belly over the top rope and leaves in a huff.  Our gals go back at it.  Eva Marie is the next entrant.  Of course she has the tedious overhype entry, but she stops at the rampway when she realizes her boot is untied.  She stays there long enough for Naomi to get her entrance.  Naomi launches the bent over Eva into the ring, only for Eva to roll out under the adjacent ropes just as Naomi reaches the apron.  Bayley and Sasha, realizing they're at a stale mate, double beal Naomi in and go after the Smackdown star.  Nikki comes into even the sides for her team, which leads to essentially tandem offense in a red vs blue stand off.  Emmalina enters and gives zero fucks about allegiance.  We'll say she gingerly tosses Nikki Bella and Bayley at an opportune moment where both are leaning into the ropes trying to get each other out.  Natalya comes out and goes after Emmalina.  Everyone squares up with a partner until Nia Jax comes out and clears out the ring except Sasha.  There's a stare down between Nia and Sasha, kind of a 'moment' toe-to-toe thing where two NXT people who never crossed paths finally run into one another for the first time.  This is when Eva makes her in-ring return, tossing the distracted Sasha over the top rope.  She signals to Nia that they're on the same page as Carmella comes out.  As soon as Eva turns to stare down the newcomer heading to the ring. Nia dumps her over the top.  Carmella acts hesitant to enter, but Nia lifts her onto the apron from the floor with a fistful of hair.  Carmella gives up a sporting, sloppy, fore arm based defense before the lights go down, Trish Stratus's music hits, and Nia flings Carmella to a corner and awaits the women's wrestling legend.  Trish goes in in full buzzsaw mode, taking it to Nia's knees with toe kicks.  When Nia has enough, she shoves her off, only for Carmella to jump in from behind and wail on her from a piggyback position.  Nia falls back and sandwiches Carmella on the mat.  As she gets up, Trish grabs her head and hits the Stratusfaction nostalgia spot.  Nia shrugs it off quickly as Summer Rae enters the fray.  Carmella and summer form a short alliance taking it to Nia.  Nia double goozles and forces both over the top rope.  Trish hits the chick kick, but Nia no-sells.  Trish goes for the Stratusfaction again, but Nia shrugs her over the top rope...right into the waiting arms of our next entrant, stalker Mickie James, dressed to the nines in Stratus's gear.  Trish looks apprehensive as Mickie holds her like a husband at the threshold.  She shoves Trish back in the ring and they go after Nia.  Chick Kick, Mick Kick, Nia's reeling as the two muscle her into the ropes and grab a leg each, trying to push her over the edge.  Paige is out next, and she's quick to grab the top rope from the outside to assist the two women's wrestling pioneers huck Nia over and out to the floor with a thud.  There's a 3 way stare down.  Trish eggs on the crowd, Mickie mimics in true stalker fashion, and Paige yells 'This is my house!' and rushes the two.  They duck the double line.  Paige ducks a Chick Kick and ducks the Mick Kick, which nails Trish in a glancing blow.  Mickie shrugs and starts doing the creepy stalker crawl toward the downed Trish.  Paige punts Mickie in the head and drops down for her own creepy stalker crawl.  She mounts Trish and lays in with a few choice headbutts.  She picks up stratus and tosses her out by the hair.  Mickie goes batty and attacks with wild rights and lefts on an on guard Paige in the corner.  Bliss makes her sly entrance, tosses Mickie, and stares down Paige as she beckons her out of the corner with her weird diamond skeletal glove.  They go at it with Paige playing face in the scenario.  Bliss hits the STK and goes up top confidently looking for the Twisted Bliss, but Paige gets to her feet and tosses her off the top and to the outside for the victory.

I would have Alexa and Charlotte as champs going into the Rumble match and getting the night off... I know two heel Main Champs is a bad idea but we slowly turn Alexa to a Face-leaning Tweener after WM33 (CUZ IMAGINE IT THE SHOOTS FROM ALEXA). 

The story going into this match from the RAW side is Bayley being soooo close to dethroning Charlotte on multiple occasions like TLC or the RAW after Survivor Series (She could be the lone survivor for Team RAW and receive a title shot because of it but Charlotte fakes an injury), another story would be something I once booked in TEW called the Bo$$ Open Challenge where Sasha would challenge any member of the RAW roster every week and even some unnamed jobbers, and every week for about 5-6 weeks, meaning she would have a crap ton of Momentum going into RR. You might ask the reason behind Open Challenge, well it's to have Sasha take a break from the title picture and let Bayley go at it plus I want to see Nia vs Sasha (If anyone can take Nia to a good match, it's going to be Sasha). 

From the SD side is Becky's road back to the top and Alexa's empire. Let's say Alexa wins the title of Becky in a tainted finish using some sort of item like Brass Knucks, because if you can put two women inside of HIAC then an outside Item finish seems tamed (I honestly feel that Becky is better when she's chasing the gold instead of holding it). So the story is that Alexa has finally started what should be a lengthy reign as women champ and she's got a crew to help her at times, like a returning Tamina who would act as her Bodyguard (Tamina could be back before the rumble with her rehab from injury) and maybe a heel Naomi... I KNOW BUT IF TAMINA IS HEEL, it would be better to pair her up with someone who she has chemistry with. So the story is pretty much Becky vs Alexa's Empire. Another part of this story is if Becky can't win the Rumble match, then she won't have another shot at Alexa till Bliss is able to drop the title to someone else.

Now during the rumble match entrance order is like this.
1. Bayley (Forced by the heel authority figure team of HHH and Steph, yes I think Foley is going to be fired before RR) (Face)
2. Dana Brooke (Yes, Dana will still be Charlotte's lap dog) (Heel)
3. Eva Marie (Heel)
4. Tamina (Member of Alexa's Empire) (Heel)
5. Lita (Surprise Entrant) (Face)
6. Sasha Banks (Face leaning Tweener)
7. Becky Lynch (Face)
8. Nia Jax (Heel)
9. Nikki Bella (Face)
10. Ember Moon (NXT Surprise AND NEW NXT WOMEN'S CHAMP) (Face)
11. Carmella (Member of Alexa's Empire) (Heel)
12. Emma (NOT EMMALINA) (Heel)
13. Blue pants (Quick Elimination like maybe a minute then super kicked by Tamina) (Face)
14. Naomi (Member of Alexa's Empire) (Heel)
15. Natalya (Tweener, right down the middle)

Notable Spots:
-Nia goes on a monster run, eliminating Eva, Dana, and Lita.
-Becky put into a three-on-one situation against Alexa's Empire but eliminates them all except for Naomi.
-Ember getting a strong showing including an Eclipse Stunner on someone, as she seems like she's on a roll out of nowhere from the crowd, a now heel Asuka to eliminate her taking revenge on Ember (I think Ember would have won via roll-up at Takeover: San Antonio).
-Nikki hits forearm smash on Nia but Jax no-sells it and is eliminated afterward (You could move Nikki to RAW and bring a new face to come over to SDLive)
-The Final Four are Naomi, Natalya, Sasha, Becky. Naomi is the first to go, followed by Natalya and then you could give Sasha and Becky about 5-8 minutes of in-ring time together and via clean finish your winner BECKY LYNCH

Elimination Order:
1.Dana (By Tamina)
2.Eva (By Nia Jax)
3.Lita (By Nia Jax)
4.Nikki (By Nia Jax)
5.Nia Jax (By Sasha, Becky, Ember and Bayley)
6. Ember Moon(By Asuka, who's not part of the match)
7. Blue Pants (by Tamina)
8. Carmella (Accidently super kicked by Tamina)
9. Tamina (By Becky right after Carmella's elimination)]
10. Emma (By Bayley
11. Bayley (By Dana and Charlotte)
12. Naomi (By Sasha)
13. Natalya (By Sasha and Becky)
14. Sasha Banks (By Becky)