Is it possible to upload multiple documents to a single catalog record (for example: an annual report)? We would like to attach many years of an annual report to a single record but the only options I see at the bottom of the record are replace or remove.

Yes, at present this seems the only option. one way around it we have used in the past is to create a field in the textbase, then add your custom UDF field to your genie config, using the TreatAs Option (to make it display as URL). Downside is you have to manually enter the URL of the document (http://genie and copy the document over to the 'DocumentFolder' (or importfolder) on the genie server manually.