We have many many problems with our WYSIWYG integration:
1. We don't support all possible formatters for files/images
2. We have major problems supporting non-image media in WYSIWYG
3. We lack the ability to set any kind of context per field
I'm attempting to propose that we focus our WYSIWYG efforts on re-using and support the WYSIWYG Fields module. All three of the above issues would be solved by using this module.
The cons to replacing our custom wysiwyg integration with WYSIWYG fields are the following:
1. More complicated set up to enable fields to be embed-able (can be helped with install/enable hooks in Media)
2. Does not support when WYSIWYG is used on a non-entity (and non-field) basis. For example, using WYSIWYG in core custom blocks.