From my perspective as both a data aggregator (e.g., BioNames) and a data provider (e.g., BioStor) there are four things I think we need to tackle in order to make significant progress.
Discoverability (strings to things)
A basic challenge is to go from strings, such as bibliographic citations, specimen codes, taxonomic names, etc., to digital identifiers for those things. Most of our data is not born digital, and so we spend a lot of time mapping strings to identifiers. For example, publishers do this a lot when they take the list of literature cited at the end of a manuscript and add DOIs. Hence, one of the first things CrossRef did was provide a discovery service for publishers. This has now morphed into a very slick search tool http://search.crossref.org. Without discoverabilty, nobody is going to find the identifiers in the first place.
Given an identifier it has to be resolvable (for both people and machines), and I'd argue that at least in the early days of getting that identifier accepted, there needs to be a single point of resolution. Some people are arguing that we should separate identifiers from their resolution, partly based on arguments that "hey, we can always Google the identifier". This argument strikes me as wrong-headed for a several of reasons.
Firstly, Google is not a resolution service. There's no API, so it's not scalable. Secondly, if you Google an identifier (e.g., 10.7717/peerj.190) you get a bunch of hits, which one is the definitive source of information on the thing with that identifier? It's not at all obvious, and indeed this is one of the reasons publishers adopted DOIs in the first place. If you Google a paper you can get all sorts of hits and all sorts of versions (preprint, manuscripts, PDFs on multiple servers, etc.). In contrast the DOI gives you a way to access the definitive version.
Another way of thinking about this is in terms of trust. At some point down the road we might have tools that can assess the trust worthiness of a source, and we will need these if we develop decent tools to annotate data (see More on annotating biodiversity data: beyond sticky notes and wikis). But until then the simplest way to engender trust is to have a single point of resolution (like http://dx.doi.org for DOIs). Think about how people now trust DOIs. They've become a mark of respectability for journals (no DOIs, you're not a serious journal), and new ideas such as citing diagrams and data gained further credence once sites like figshare started using DOIs.
Another reason resolvability matters is that I think it's a litmus test of how serious we are. One reason LSIDs failed is that we made them too hard to resolve, and as a consequence people simply minted "fake" LSIDs, dumb strings that didn't resolve. Nobody complained (because, let's face it, nobody was using them), so LSIDs became devalued to the point of uselessness. Anybody can mint a string and call it an identifier, if it costs nothing that's a good estimate of its actual value.
Resolvability leads to persistence. Sometimes we hear the cliche that "persistence is a social matter, not a technological one". This is a vacuous platitude. The kind of technology adopted can have a big impact on the sociology.
The easiest form of identifier is a simple HTTP URL. But let's think about what happens when we use them. If I spend a lot of time mapping my data to somebody else's URLs (e.g., links to papers or specimens) I am taking a big risk in assuming that the provider of those URLs will keep those "live". At the same time, in linking to those URLs, I constrain the provider - if they decide that their URL scheme isn't particularly good and want to change it (or their institution decides to move to new servers or a new domain), they will break resources like mine that link to them. So a decision they made about their URL structure - perhaps late one Friday afternoon in one of those meetings where everybody just wants to go to the pub - will come back to haunt them.
One way to tackle this is indirection, which is the idea behind DOIs and PURLs, for example. Instead of directly linking to a provider URL, we link to an intermediate identifier. This means that I have some confidence that all my hard work won't be undone (I have seen whole journals disappear because somebody redesigned an institutional web site), and the provider can mess with different technologies for serving their content, secure in the knowledge that external parties won't be affected (because they link to the intermediate identifier). Programmers will recognise this as encapsulation.
Some have argued that we can achieve persistence by simply insisting on it. For example, we fire off a memo to the IT folks saying "don't break these links!". Really? We have that degree of power over our institutional IT policies? This also misses the great opportunity that centralised indirection provides us with. In the case of DOIs for publications, CrossRef sits in the middle, managing the DOIs (in the sense that if a DOI breaks you have a single place to go and complain). Because they also aggregate all the bibliographic metadata, they are automatically able to support discoverability (they can easily map bibliographic metadata to DOIs). So by solving persistence we also solve discoverability.
Lastly, if we are serious about this we need to think about how to engineer the widespread adoption of the identifier. In other words, I think we need network effects. When you join a social networking site, one of the first things they do is ask permission to see your "contacts" (who you already know). If any of those people are already on the network, you can instantly see that ("hey, Jane is here, and so is Bob"). Likewise, the network can target those you know who aren't on the network and prompt them to join.
If we are going to promote the use of identifiers, then it's no use thinking about simply adding identifiers to things, we need to think about ways to grow the network, ideally by adding networks at a time (like a person's list of contacts), not single records. CrossRef does this with articles: when publishers submit an article to CrossRef, they are encouraged to submit not just that article and it's DOI, but the list of all references in the list of literature cited, identified where possible by DOIs. This means CrossRef is building a citation graph, so it can quickly demonstrate value to its members (through cited-by linking).
So, we need to think of ways of demonstrating value, and growing the network of identifiers more rapidling than one identifier at a time. Otherwise, it is hard to see how it would gain critical mass. In the context of, say, specimens, I think an obvious way to do this is have services that tell a natural history collection how many times its specimens have been cited in the primary literature, or have been used as vouchers for DNA seqences. We can then generate metrics of use (as well as start to trace the provenance of our data).
I've no idea what will come out of the TDWG Workshop, but my own view is that unless we tackle these issues, and have a clear sense of how they interrelate, then we won't make much progress. These things are intertwined, and locally optimal solutions ("hey, it's easy, I'll just slap a URL on everything") aren't enough ("OK, how exactly do I find your URL? What happens when it breaks?"). If we want to link stuff together as part of the infrastructure of biodiversity informatics, then we need to think strategically. The goal is not to solve the identifier problem, the goal is to build the biodiversity knowledge graph.