I have issues with the endings and I'm sure you do too. *Spoilers*
Let's look at them.
Go Alone.
Clementine, whose like 11/12, WILL NOT survive alone with a baby who will easily attract walkers because let me tell you this - Babies can be VERY loud when they're hungry. Heck she nearly died from a dog bite when she was on her own, there's no way she'll be able to raise a baby when she has no food, supplies, a plan or even how to care for a child. And if that Baby gets sick or decides to scream at the worst time? Yeah... Furthermore, if you ditched any of the survivors you signed their death warrants as well since Kenny wants to die, and has wanted to die since Duck died, thus he will kill himself and Jane, who would has no reason to live if Clementine leaves her, will kill herself if Clementine leaves her. By choosing this ending you've killed everyone. Are you happy?
The only way this works out is if a magical fairy waves their wand and makes the Baby NOT act like a Baby and Clementine's survival skills are GREATLY exaggerated to the realm of impossibility.
Go to Wellington
You know NOTHING about this place other than it has an overpopulation and supplies issue, for all you know this could be another Crawford(Gave strong vibes of that) or is run like an insane dictatorship like under Lily, Kenny, Carver, and the Governor where if you aren't in line you could very well be murdered in cold blood. Kenny also will commit suicide after seeing you off since without the Baby in his life he will see no reason to want to carry on. That and YOU let him become the next Lily/Carver/Governor by not stopping him from murdering Jane. Kenny cannot live with himself after committing cold blooded murder, as that's not the type of man he wants to be nor would his family approve, and the Baby is the only reason he doesn't kill himself outright.
The main point here is you're given NO information about this place at all and you're supposed to believe it's so awesome when the signs point to it not being the pretty picture Kenny thought it would have been. Huge leap of faith there. They should have shown you actually inside the place and get a good view on how things are so that you can have SOME hope that it may work out for Clementine despite the warning signs about the place.
Go with Kenny
Kenny wants nothing more to die and is a walking time bomb. Murder becomes easier after the first time and killing Jane is the first time that Kenny intentionally wanted and did kill an innocent life thus turning him into the thing he hates - a Monster. He's no better than Lily, Carver, or the Governor at that point. Going with him means that you will never find yourself in another secure group, especially since Kenny is the main reason for why your last group went to heck. He's simply not a people person and he lashes out against nearly everyone and is always quick to start fights instead of thinking rationally.
Furthermore when the Baby gets ill, and he will as everyone gets sick eventually especially in such a ruinous world, Kenny will freak and if the Baby ends up dying you can BET that Kenny will end up in a Blood Rage, and trust me he WILL rage if the Baby dies, and will end up accidentally attacking and possibly killing Clementine due to him failing the Baby if she's the only one around. After his rage leaves he would commit suicide as he would never be able to forgive himself even if Clementine survives. Thus leaving Clementine on her own, if she isn't killed by him, with raw chances of any survival unless she manages to find and piggybacks onto another group like she did at the start of Season 2.
Finally, Kenny doesn't teach Clementine how to survive, and underestimates how independent she is, and isn't the smartest guy around which others have pointed out and even Kenny knows this. Compared to Jane he wont be able to prepare Clementine for a time when he isn't around. Remember, Kenny is also badly hurt by the end of Season 2, he isn't really all that strong/healthy anymore both physically and mentally, and he's pretty old as well as being highly suicidal and doesn't even want to live after murdering Jane in cold blood. Than the Blood Rages... I fear for any Clementine that stays with him, heck even Kenny is scared over what he's become hence why he WANTS Clementine to leave him so he can kill himself as he knows he's a danger to Clementine and the Baby.
Jane and The Family
Not ONCE are you allowed to question the family about these things which makes letting them in extremely irrational as you learned nothing from Lee and puts both Clementine and Jane's lives in danger.
- How is that your son? What is your relation? Please tell me the truth, family doesn't have to be about blood.
- How long have you all been together? How'd you all meet up?
- What's happening out there, any news at all?
- Were you in a group before? What happened to them?
- Do you have any weapons? Show them to us as a sign of good faith and take out the ammo in any guns you have. If you lie to us...
- Call out the man when he aggressively pulls his arm away from the woman which leads her to cast her eyes down in submission. That is a CLEAR sign of an abusive relationship and that he sees himself as an Alpha. It's the whole "Shut up! You don't get to speak, only I do, unless I tell you to speak!" thing. See how he reacts, if he acts overly aggressive over this instead of calmly trying to explain that he's merely under a lot of stress than you'll know what type of man he is and whether you should let him in or not.
- Point out that you're calling the shots here, not the man who seems to want to be the one in charge and appears dismissive to the woman's opinions.
- Suggesting that you may only let the Woman and Child in, see how they react to that.
Letting them in
When you let them in the man walks in like he owns the place and doesn't really acknowledge Clementine or Jane while the woman and the kid move to try and distract you. Notice the look the child gives when he notices that Clementine turns from him back to the man's gun. To me it seemed like they planned to take over the place, or at least the man wants to take control as he's a huge Alpha, and the woman and child are merely working with him due to being submissive to his domineering personality and Alpha Status. I, for one, fear for Clementine and Jane as that man may attempt to take control sooner than later and attempt to murder or even rape Clementine and Jane to establish his role as Alpha and to deal with threats to his dominance.
Furthermore, you don't have the option to immediately pull out your own weapon and tell the man to hand over his weapon and that he'll only get it back when he's earned your trust. Than telling him that if he hadn't kept the weapon a secret, thus not having your trust, he would have been allowed to keep it. If the man refuses to hand if over you should have been given the option to shoot him and than decide whether the woman or child can stay or not.
Sending them away
If you don't let the family in you will have issues with keeping the place running and secure, furthermore the man may return and try to attack the place in the future since he doesn't seem the type to accept that a little girl tried to order him around. You also don't have the option to tell Jane that you sent them away because you felt that man is dangerous and you don't get to tell her that you will let in or turn away people on a per person basis and that you aren't trying to isolate yourself from the world.
Out of the endings this one at least has a future you can predict somewhat and know that Clementine is safe and Jane will continue to teach Clementine and will protect her. Jane is even willing to let others in her life if Clementine approves. This makes Jane reliant on Clementine, though, but it ensures that Jane isn't suicidal and she wont abandon her own reason for living - Clementine.
Another issue is that it SHOULD have been Kenny vs Luke or Kenny vs Luke/Jane - Luke believing Jane and not agreeing that Jane should die.
Luke was built up from the first episode, killing him off seemed like you wanted to make those that choose Kenny feel better about committing murder and becoming the next Lily/Carver/Governor. There's no doubt that Luke would have defended Jane from Kenny and if it was Kenny attacking Luke, who would be truly innocent as Jane wouldn't tell him her plan, it would be MUCH harder for Kenny fans to say Kenny's right for committing cold blooded murder and they know it. So instead Telltale brings in Jane back in only to try and make Kenny fans feel better about siding with someone whose no better than Lily or Carver at the end of Season 2.
After choosing Luke and Kenny saying you're right it should be revealed that Jane was lying and having her freak out that she didn't think it would have got all out of hand. At that point Clementine should choose to forgive Jane or not with Luke deciding that he will go with Clementine, if Clementine will let him come, whether she forgives Jane or not. If Clementine ditches him he has no choice but to stick with a now suicidal Jane, as he knows he wont survive alone and he'll want to try and save someone, but he'll respect Clementine's decision.
Speaking of which, Jane was given far less lines and explanation than Kenny and you aren't allowed to agree that Jane was right about Kenny being a walking time bomb. It's clear that Kenny was planned as one of the end choices but Jane wasn't, it was supposed to be Luke or Luke/Jane. To me it seemed like you freaked, when fans started harping about Luke vs Kenny, and wanted to instead pull a surprise as well as make the Kenny choice look somewhat tempting (As Kenny vs Luke/Jane would have been players OVERWHELMING picking Luke and giving Kenny the peace he wants) and the only one you could use for that is Jane considering that fans seemed to like her somewhat, unlike Boonie, from previous episodes due to her training Clementine and bonding with her.
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The only highlight in my eyes in regards to the endings is that Kenny realizes, after you shoot him, that he was close to crossing the line and that you stopped him which he felt was the best decision you could have made in the situation. That shows that Kenny wasn't truly gone in his last moments and that he's thankful that you stopped him from murdering Jane and becoming no better than Lily/Carver.