+ AA6YQ comments below
Balancing the integrity of DXCC and other awards vs. simplicity and immediate response is where you and the other Directors will ultimately decide. You can pull it towards simple or towards secure. I don't have any obvious answer.
+ LoTW is difficult to use because a well-meaning but naïve ARRL management were convinced in 2001 that one developer could implement, test, and document LoTW in 9 months. To limit the schedule slip to a couple of years, that developer threw everything overboard that he didn't consider essential -- like testing, documentation, and a user interface that hide the implementation details and security mechanism from users. For example, there's no reason for users to be aware of - much less have to manage - Callsign Certificates. An international online confirmation mechanism that can't be localized to languages other than English is absurd.
+ In 2013, the ARRL Board approved the hiring of two software engineers to improve LoTW's availability, reliability, and usability. Good progress was made against the first two, but in 2017, those engineers were re-assigned to other projects - one of which failed outright, and the other of which now makes it possible to "renew, purchase, and donate in a single transaction". As a result, there have been no subsequent improvements to LoTW's usability or functionality in more than 5 years.
+ A "total redesign" of LoTW would require ARRL staff to support the current implementation for years while designing, implementing, testing, and documenting its replacement; this would be a challenging project for an organization well-skilled in modern software engineering; an organization that took four years to roll out a commercially-supplied software package (Personify) and then failed to realize that its password rules were inconsistent with those of the system it replaced has little hope of succeeding.
+ The better approach: design a modern new user interface that can be localized by volunteers, and deploy it incrementally in the current implementation of LoTW, soliciting user feedback as each new section is rolled out and making course corrections based on that feedback. Re-hosting the LoTW Server to the cloud for access to additional computing resources during peak periods (like after popular contests) would be a reasonable "next step" after the usability issues have been eliminated.
73,
Dave, AA6QY (member ARRL LoTW Committee, 2012-2017(