See Learning Dojo as a reference for a curriculum.

The basics

WO/Learning+WebObjects
WO/WO+5.4+Getting+Started
WOL/Tutorials
WO/Development-Beginner%27s+Guide
WO/Documentation (WebObjectsOverview.pdf, WebApplications.pdf, EnterpriseObjects.pdf, UsingEOModeler.pdf, DynamicElements.pdf)
http://web.me.com/pccdonl/tutorials/EoModelBasics/EoModelBasics.htm
http://media.libsyn.com/media/dickwall/JavaPosse005.mp3
http://webobjects.mdimension.com/wonder/screencasts/ERRest-2010-02-16.mov
http://www.wocommunity.org/podcasts/Component_Editor_Howto.mov
http://www.wocommunity.org/podcasts/UI_overview_of_WOLips.mov
http://www.wocommunity.org/podcasts/WOWODC08_BestPratices.mp4

Project Wonder

http://www.wocommunity.org/podcasts/wowodc/2010/GettingStartedWithWonder.mov

Advanced

http://www.wocommunity.org/podcasts/wowodc/east09/WOWODC09E-Components.mov
http://www.wocommunity.org/podcasts/wowodc/east09/WOWODC09E-EOEnterpriseObjects.mov
http://www.wocommunity.org/podcasts/WOWODC09E-ThisYearModel.mov
Practical WebObjects
http://www.wocommunity.org/podcasts/WOWODCW09-TDD.mov
http://www.wocommunity.org/podcasts/wowodc/west09/WOWODCW09-InsideEOF.mov
http://www.wocommunity.org/podcasts/wowodc/west09/WOWODCW09-Localization.mov

Web Services

WO/Documentation (WebServices.pdf)
ERRest 

D2W

DevelopingWithD2W.pdf
http://www.wocommunity.org/podcasts/ERModernDirectToWebIntro.mov
http://files.me.com/dav1d/bkjjeo.mov
http://www.wocommunity.org/podcasts/WOWODC09W-D2W-part1.mov
http://www.wocommunity.org/podcasts/WOWODC09W-D2W-part2.mov

Deployment

DeployingApplications.pdf
http://www.wocommunity.org/podcasts/wowodc/east09/WOWODC09E-Deployment.mov