Here you can find several educational links that will step you through transforming elevation data with VDatum, provide brief introduction to datums, and much more.
Estimation of Vertical Uncertainties in VDatum
Frequently Asked Questions: such as why VDatum gives me -999999, etc..
User Guide: this page will guide you through all steps to transform an elevation data point or dataset with VDatum user-friendly interface.
Command-line Guide: an instruction of how to run VDatum as a command.
A brief tutorial about datums: a brief introduction of datums that are supported in VDatum.
Extra tutorials provided by NOAA/NGS about geodetic and tidal vertical datums
"Webinar, presented August 16 and 18, 2011.", by Dave Minkel, Michael Michalski and Scott Duncan
"Webinar, presented March 2-3 and 9th, 2010.", by Dave Doyle, Gerald Hovis and Cristina Urizar