So, I’m going to try to guess Desmond’s pup, and you know me, I tend go on long winded tangents and end up in left field a lot. But I am kind of liking left field more and more since I spend a lot of time here. It’s actually quite peaceful out here. Someplace to kick back, relax, and watch the clouds go by, and maybe a hint or 2. I just hope my head isn’t in the clouds....
1. Desmond's signature has the words in small text,
"I am very particular with my words." This was restated over and over many times as well.
2. From Page 345
Desmond wrote:I'm having a meh day at work, so I'll just... Drop a vague direction to another clue and see where that goes.
Look where you have looked before. I watch where you go and lay things behind you -- so they may stand out when you backtrack, to lead you where you need to go.
3. Desmond’s comment
not link to Shobits' post about a pet named Mr. Miles in one of Desmond's groups on page 352
Desmond wrote:Shobits wrote:Desmond
This little dress-up in your ungrouped pets named Mr. Miles wouldn’t happen to be a hint, would it?

And looking back where we’ve looked before might relate to the stories of your previous staffs.
While this year may or may not continue the air, water, earth, and fire theme... if it does I think spirit is next.
He'll get you just about there. Right universe, at any rate.

...and I didn't actually think about that, but... You might be right, there, in a very strange way. I don't consciously follow that idea, though, so who really knows. XD
So I backtracked on Discord and I found various conversations going on. Here are things Desmond said as responses to various questions or in conversations.
Does your puppy have any yellow on it? - “idk. right now it does, I guess” and “sure in the stage it is in, it has yellow”
A link to Desmond Miles of Assassin’s Creed -
https://i.pinimg.com/originals/53/0d/8d/530d8d612f77c0f711c9584c117d4656.gifPart of Shobits questions and answers session with Desmond
S: Looked over some past Discord posts since you said you are very *particular* about your words, so these questions may seem odd. 1. Does Assassin's Creed link to your pup or just your name? Snip
D: 1. Hmm. It's quite possibly linking to something. Look into it a bit more and broaden those horizons. Snip
As well as these responses
I don't only play AC
I play other games
Ubisoft seems to especially own my soul.
You're going in the right kind of direction, though.
keep going
Looks like the dominant guess for me is the "dinosaur" pup, yeah? No other guesses yet?
ouo b
Just checking
For science
It's science so long as it's written down.
Here is my thoughts on the above hints and the pup I believe is yours as a result.
Some of your hints pointed to Assassin’s Creed - the post of Desmond Miles and the controller which I think was meant to look at Desmond Miles and not Assasin’s Creed. When asked if your pup has something to do with Assassin’s Creed, you answered rather vaguely - “Hmm. It's quite possibly linking to
something. Look into it a bit more and broaden those
horizons.” You never actually said it was linked to Assassin’s Creed. You backed this up by saying you also play other games. Again, you are “...very particular with my words.”
Then you asked if there were any other guesses besides the “dinosaur” pup. You were “Just checking For science” and “It's science so long as it's written down.”
I then looked at Shobits finding Mr. Miles. Your response to him being a clue:
“He'll get you just about there. Right universe, at any rate.

”
Notice that Both Desmond Miles and Mr Miles both have Miles in there names? And science would say things about how Cumulus clouds can also develop in layers. Stratocumulus is a layered cumulus cloud about a mile above the ground. Altocumulus is a similar cloud at an altitude of 2 miles... which, of course, is written down.
So with these hints and my assumptions, I think this pup is yours. It looks like ther are cumulus clouds with a yellowish hue surrounding them floating in the sky.

The End
I hope you enjoyed my long winded explanation. And if I’m wrong, I hope I found a missing hint somewhere up there. Now to keep watching the clouds go by... ☁️ ☁️ ☁️