Think of an imaginary sibset of 4 kids. Which would be worse: all 4 names starting with the same letter, or all 4 names ending with the same letter? Here is an example:
Same Starting Letter:
ds: Teddy
ds: Tate
dd: Tessa
dd: Teagan
Same Ending Letter:
ds: Otto
ds: Enzo
dd: Cleo
dd: Margo
My thoughts
I think starting with the same letter is worse, though both get ridiculous if you have lots of kids. However, I have met several wonderful families who started their kids names with the same letter, which I don’t like stylistically but I know some people love it 
Although I’d personally wouldn’t choose either, I think starting letter is much better than ending letter. At least with starting letter, you can vary it a little bit and they don’t sound the same other than the first sound. I also think there are plenty of wonderful names that start with a few letters. The ending letter sounds sing-songy and it would get a little much over time imo.
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I think the stereotypical matching sibling names thing to do is the same first letter approach, which has always felt pretty cheesy to me, so I’m not a fan of it. Matching last letters are less common (I don’t think I’ve ever encountered it?) so it doesn’t have that same cheesy feel to me!
There’s also the fact that if you have siblings named Jason, Jaden, Jeremy & Jolie, I absolutely will notice it & assume the matching J initials were intentional. But let’s say you have siblings named Ben, Ethan, Lillian & Evelyn. I may not even notice the matching -n endings right away, and even if I did, I wouldn’t be sure if it was done on purpose, or if the parents simply liked all these -n names. So I definitely prefer that!
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I think all names having the same first letters is worse. It’s very obvious and matchy. The same ending letter is more subtle.
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Definitely using the same first letter is worse – overdone and is very extreme as the number of children increases.
I think it depends on the letter; I would personally opt for ending letter over starting, though maybe not with a letter as memorable as “O”. For instance, I would prefer [name_f]Grace[/name_f], [name_f]Louise[/name_f], and [name_f]Charlotte[/name_f] to your example, though both are nice. I think starting is worse because then you get caught into a pattern.
Tough, because it’s going to greatly depend on the letter 
What I mean is, with your example, I prefer the same initial - the names otherwise sound distinctive and there are plenty of T names to choose from, whereas -o endings aren’t as popular where I am, so it feels rhymey, deliberate and a bit much for me.
However, other sets would make me feel differently:
Something like [name_m]Nathan[/name_m], [name_m]Hudson[/name_m], [name_f]Erin[/name_f] and [name_f]Megan[/name_f] work better than [name_f]Xena[/name_f], [name_m]Xavier[/name_m], [name_m]Xylon[/name_m] and [name_f]Xanthe[/name_f] to me, but [name_f]Sarai[/name_f], [name_m]Sylvan[/name_m], [name_f]Saskia[/name_f] and [name_m]Solomon[/name_m] are better than [name_f]Cherith[/name_f], [name_f]Delyth[/name_f], [name_m]Griffith[/name_m] and [name_m]Kenneth[/name_m] (but [name_m]Ezra[/name_m], [name_m]Luca[/name_m], [name_f]Maia[/name_f] and [name_f]Thea[/name_f] are better then [name_m]Ezra[/name_m], [name_f]Esme[/name_f], [name_f]Erin[/name_f], and Evan)
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I think it depends on the letter!
Some letters have different sounds, so as a first initial they still work even. I’m thinking of A - [name_f]Alice[/name_f], [name_f]Audrey[/name_f], [name_m]Adrian[/name_m] and [name_m]Ari[/name_m] all have a different starting sound even though they start with the same letter, and I think they work together quite well. C is another one - [name_m]Casper[/name_m], [name_f]Chantal[/name_f], [name_f]Cecelia[/name_f] and [name_m]Charles[/name_m] are also fine.
-a, -y and -n as endings also would be fine, because there are so many common names that end with those letters. But the more unusual endings like -o, -x, -z etc stand out a lot more and don’t work as well when used for a whole set of siblings.
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It would depend how forced it felt, and how much I liked the individual names. But I think the same starting letter would usually be worse.
For your particular examples, I like the second set better, but that’s because I love [name_m]Otto[/name_m], [name_m]Enzo[/name_m], and [name_f]Cleo[/name_f].
I would much rather have a set with the same ending letter than the same starting letter! Especially as I think oftentimes having the same ending letter is something that comes naturally and coincidentally, while the same starting letter is usually something people look for, and I find the “randomness” cute!
It very much depends on the letter and names, but there’s something about names with the same ending (excluding -a endings, silent e, and maybe -n) that makes them feel so much more similar. Maybe because it’s the last thing you hear, or they’re more susceptible to rhyming, my brain just notices it more. Whereas names with the same initial letter usually sound much more different to me. -To, -go, and -zo rhyme, whereas Te-, Ta-, and [name_f]Tea[/name_f]- don’t.