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I don't think I'd ever do this because I prefer short forms over diminutives by a lot. I think Molly is cuter than Mary. Sarah is prettier than Sadie, but I prefer Sadie to Sally. I love Henry but dislike Harry. A lot of such names are Biblical and very, very common. I avoid common names, so it's unlikely to come up with my own kids.

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Nicknames I like that have less syllables:
Mackenzie - Mack or Kenzie
Jason - Jay or Jace
Mason - Mace
Joseph - Seph
Nathan - Nate
Oliver - Olly
Alexander - Alex or Xander
Caroline - Carrie
Tatum - Tate
Theodore - Theo
Joshua - Josh

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Nicknames I like that have the same number of syllables or more:
Linda - Lindy
Ella - Ellie
Braden - Brady
Rose - Rosie
Anne - Annie
James - Jamie

Flora and Molly are very cute. I like them a lot.
If more Sarahs went by Sadie, I would know a lot less Sarahs.

I think a lot of us tend to think of nicknames as "short for" when they aren't necessarily for that purpose. In ye olden days, there were so many people who had the same name that nns were used too distinguish them from each other.

These make more sense when you consider the limited pool of names people were drawing from. They’re not shortenings so much as distinctions - when you’ve got generation after generation where everyone’s first born is Henry, for example, you end up calling them all sorts of nicknames to clarify who you’re talking about.

The multitude of nicknames came as a way to differentiate people who had the same name. In the old days, people named children after family members, mostly; they didn't have access to a huge pool of choices, and unique names simply weren't as fashionable then. So you'd have papa Henry, Grandpa Henry, Henry Jr and cousin Henry all in the same family. Much easier to tell them apart if they are Henry, Harry, Hal and Hank.

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I think the two syllable thing is simply because we seem to love those kinds of names through human history. Look at the popularity charts, we still love them!

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Sure I'd use a nickname like this for a child. I like lots of nicknames. I'm especially fond of all the short forms of Margaret - they're all great.