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Since you claim to be eager to learn....the term "transgendered" is outdated and out of favor with the trans community. That's actually poor grammar. It would be similar to me saying I'm "Irished" or "whited."

If you want to read more on that:

https://www.plannedparenthood.org/learn/gender-identity/transgender/transgender-identity-terms-and-labels

https://www.vox.com/2015/2/18/8055691/transgender-transgendered-tnr

This one even includes a helpful section entitled, " Basics of writing a transgender story:"

https://www.glaad.org/reference/transgender

As to your examples, which honestly seem like you are deliberately using poor grammar:

"Jerry wrapped their hands around the coffee cup." Not difficult.

My standard reminder - it is not the job of marginalized people to educate you. Some choose to do so, but it should not be an expectation or requirement.

Fun fact, I noted that you claim age as ignorance to the use of the singular "they." The use of singular "they" has been around since the 1300's.

The pronouns you use for people are the ones they ask you to use. Nothing more or less. Most transgender, genderqueer, and non-binary people are very understanding that people have difficulty remembering pronouns at first. If you slip up, just quickly correct it and move on. No big explanation or lengthy apology. And certainly don't make a big speech about grammar. Transgender folks are not asking for your grammatical blessing (which would be moot, since singular "they" is not incorrect. They are asking you to treat them as humans and identify them the way they ask.