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Since inviting external users to your SharePoint site is painful when you're using on-premises, what ways do you suggest I share information with external users? I'm looking to share the contents of document libraries mostly.
EDIT: I've seen the suggestion to create an extranet site, but I'm unsure of how to go about doing this.
For SharePoint on-premise, the "real" way to handle collaboration with externals is to meet them halfway - literally! What I'm referring to is an extranet space.
Bill Baer of Microsoft has blogged about the subject in layman's terms by the blog post SharePoint Server 2013 Extranet and Office 365 External Sharing Considerations.
As the blog points out, the starting steps would be to get introduced to the following articles:
The biggest disadvantage with extranet-spaces is the pre-configuration required to have your site/space up and running. After that, the administrative perspective is as effortless as it gets in SharePoint, so there's not much to do once you are on the site.
Another considerations I could name would be to handle the documentation through a shared OneDrive, or through a specifically set up O365 environment. These are likely to be less synchronized and connected to your on-premise environment, but then again are more designed for collaborating with externals.
If only a few people need to share with external users, then putting things in Office 365 is a cheap option. Store things that need to be shared on O365, and everything else can stay on prem.
Another option that is technically feasible, though IT will say no, is to create domain accounts for those users, and allow them to access the site the same as other users. Clearly, this has some pretty significant security implications, but sometimes "external users" are long-term, trusted individuals whom IT doesn't mind giving an account.
edit: if you want to go the official route of setting up an extranet site without giving users AD accounts, an excellent resource is the SharePoint FBA Pack, located here. Be sure to see the "important" section, as it has a link to an excellent guide for configuring SharePoint for Forms authentication. This is not a simple thing to set up, and there are quite a few challenges for using it. As a result, my current preference is the separate O365 site, but again, the FBA authentication works as well for an on-prem solution.
We use a product called AvePoint Perimeter to do this.
Perimeter has a site feature that you install on your SharePoint servers, that when activated, provides an option to share files or folders in document libraries with external users.
The other component to it is a "gateway" server that you set up that must be externally accessible (http or https) and it handles authentication of external users (by their email address, self-service account creation, two-factor auth, etc.) and surfaces the SharePoint files/folders you shared with them. It acts as a conduit between the external users and your internal SharePoint. External users never have direct access to SharePoint.
