These items all have a varying level of "Business Value" (value) associated with them - but are sat in the system. They are all blocked by the same thing - the legacy system has a quarterly release cycle.
This poses a couple of questions:
- Is there a threshold before the amount of value being delivered outweighs the cost of putting that value live?
- Should every single piece of item developed be pushed live as soon as it is ready - therefore giving you an instance ROI?
- Are the items of high enough value to the customer if they can just sit in the "Done" column for a couple of weeks?
- Do the customers have visibility of what is "Done"?
My gut feel is that the first question is a cop out - the cost of pushing things in to a live environment should be minimal because you should really have seemless CI. It should be of no extra cost to put code in to a live environment. If it costs - you need to spend time & money on improving this build & deploy system. This is an Internal Quality as Martin Fowler puts it.
If you push every single piece of work live you need to have customers who can accept a constantly changing system. This maybe difficult but I think it depends on what you are delivering - i.e. defect fixes, and minor enhancements could be dropped in at any point. With large changes in functionality - it depends on how involved the customer has been with the development. Here we probably can't do it, because the customer is not overly involved.
The above statement probably answers the last two questions as well. It's all about the customer deciding on what to develop - this way they can decide upon the items with the highest value. They also know when items are complete.
This is one of the 4 principles in the Agile Manifesto - "Customer Collaboration".