I was finally able to upgrade a custom fields install from mt 4.0 to mt 4.1 then to mt 4.2
This workflow was helpful, but not successful for me:
http://www.movabletweak.com/app/migratingcustomfieldsmovable_type.php
Here's the route that I took, with help from tech support:
- duplicated the mysql database of original MT 4.0 install
- uploaded the 4.1 to server
- unzipped the install on the server
- moved the mt-static directory to a new clean directory in the site root
- updated the config file to point to the new mysql database * IMPORTANT *
- Do not copy over the OLD CUSTOM FIELDS PLUGIN
- logged in to the new 4.1 install (this prompted a database upgrade)
- once the upgrade was complete THEN copied the CUSTOM FIELDS UPGRADE ASSISTANT PLUGIN to the CGI-BIN/MT/Plugins directory
- logged in to the new 4.1 install again. This again prompted a database upgrade for Custom Fields Plugin Upgrade Assistant
- it ran the the upgrade successfully.
If you are having trouble downloading the Upgrade Assistant Plugin from the developers site here is a direct link to the zipped file: http://code.sixapart.com/trac/mtplugins/changeset/590/branches/CustomFieldsUpgradeAssistant-bugfix?old_path=%2F&format=zip
Reported on Movable Type 4.0x

Interesting. Can't say that I had any upgrade problems going between 4.1 and 4.2, but good to know.
Just to clarify, this was using arvind's original third party Plugin, not the Plugin that is part of the Professional Pack from Movable Type.