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Some Context: Most of my onboarding is not teaching others to create sheets, but to use created sheets.

• How do you usually onboard new people? Most users in our company only interact with Data intake Forms. If a user is in a role where they need to maintain or update the sheet, I normally have created a guide around the process, and talk them through in person on how to use the sheet.
• What is the single biggest struggle? Wording is crucial to get right. What might make sense to you, might mean something different to someone else. Don't be afraid to adjust wording and use in the first few works of implementing a new project. Once a project is established (1-3 months), be very careful to make big changes as will need to retrain all who use it.
• If you could snap your fingers? On hover details for each column or even cell I could add extra help into. More places to put guides directly in Smartsheet rather than outside of it. In sheet training would be much easier to role out to users.

Again, this is from the perspective of someone who creates sheets, and onboarding is for users, not others creating in Smartsheet, but hope it helps.