Hi,
The only way I know to make this part simpler for the end-user is our product DocumentsCorePack and/or AutoMerge.
With this products you are able to generate complex quotes or other documents with a single click or with AutoMerge in the background in a workflow or dialog.
If you are interested, you can go to www.mscrm-addons.com and take a look or download our test version.
Christian Ternek, www.mscrm-addons.com
follow us twitter.com/mscrmaddons