Well, the question here is how long ponies live, in a stable. Grannysmith can be a few hundred years old, so this head cannon might work. But even if they live longer than us, question: How old they bear their foal.
But yeah, according to our world’s standards they would live 20-30 years, or so: this family tree definitely ought to be longer.

Someone should make a family tree like this except replace fallout equestria with generation 5.

The different sizes of the question marks, and also the missing question mark, is annoying me greatly.

@Vree  
Hm, could have sworn it was in the fic, but that’s the version of events from the Ask Ghoul Ditsy tumblr, which is one of the three or so FoE tumblrs that might as well be canon.

@Vree  
It actually doesn’t say anything about Dinky being at Littlehorn, though as you said, it doesn’t really invalidate that.

@wselfwulf  
She has more grandparents that just 2, there 2^X grandparents where X is every generation between them and the offspring. Lineage is more a matter of which ancestor of many you consider important.
 
@FancyCat2008  
That is interesting. Does it actually say that? I thought Dinky wasn’t even mentioned.  
Technically it does not neccessarily invalidate the possibility, even if we hold that option, since at the time of the story, Dinky would have been an adult teacher and may already haver had children. But if one prefers her to be offed in that manner (in a representation of lost innocence or whatever), that is a suitable end too.

@wselfwulf
 
And it is pretty strongly implied through Pip’s genetic disposition to addiction that she would be Berry Punch’s great-great-great-great-great-great-great granddaughter. Provided there’s no other alcoholic pone in Ponyville.

one side of this is wrong as its reveled in chapter 28 that steelhooves is both littlepip and Velvet Remedy’s Distant grandfather, descended from a foal he had with applejack but littlepip being descended from berry punch could still work as a headcannon.

Kinda looks like Berry is eyeing Derpy…Is one the parent of the other’s child?
 
D: “I just don’t know what went wrong…Seriously, I don’t, this shouldn’t even be possible.”
 
B: “Don’t look at me, I barely remember that night.”

I think it’s meant to be heavily implied that Berry Punch was an ancestor of Littlepip, considering her mother and her “special talent”…
 
But there’s no way she’s related to Dinky. Dinky died at Littlehorn.

@Background Pony #92B4  
There WAS a headcanon where Pierce was considered for both Dinky’s and Ruby’s father…Yes, your idea works. :p (Not that it has to be Pierce, it can be anyone)

@Antonyourknee
 
Four generations would be roughly a hundred years, and not the approximately two hundred years time difference in FoE.
 
Not to mention I believe it was mentioned that everyone in Pip’s stable would ultimately be one part Applejack in some fashion at some point.

@Background Pony #92B4  
That wouldn’t really change anything would it…the male slot for both of them is left blank so it might very well be that.

Such a lovely headcanon… wonder how it could be improved on?  
I know!  
Bahahaha!  
 
_{obligatory naughty content warning  
[spoiler]It’d be so cute if Berry and Derps had the same partner!  
A nice, necklace-shaped family tree!} [/spoiler]

@Background Pony #D621  
Yes. Applejack is in Pip’s tree but… considering the fact she’s a unicorn AND a runt.. it’s probably a very VERY small amount of Apple family.

Isn’t Pipster related to Apples, though?
 
(And why do that if you don’t even like the fic?)

@Antonyourknee  
In a word? No. There are two hundred years to span here. But this works as the top and bottom of a longer family tree.

I can get behind this. Headcanon accepted!

@Starswirl  
Sweet Apple Acres must’ve been full of them, so I imagine that shouldn’t be a problem

You need to put an Apple in there somewhere. She’s one of Applejack’s descendants, like most of her stable.

See, the cool thing is that not only ties her name and small size to a clear ancestry, but it means she’s been adventuring with her great-great-…-grandmother without even realizing it. Which is kinda cool.
 
Of course, it can be questined how much this really matters, since if you assume enough generations in-between, then any major bg pony would have had a chance to contribute to Pip’s geneology :p

Could four generations bridge the gap between the fallout Equestria time difference?