Staying on an old version of a product has a cost.

Any cost/benefit analysis about moving to a new version of a product should include the costs of staying on an old version, otherwise it is not a blanced analysis.

New versions of products such as SQL Server tend to be more reliable than older versions. This means less unplanned downtime. This mans less cost to the business.

New versions of 'interesting' produts such as SQL Server help in staff attraction and retention. This means less recruitment. This means less cost to the business.

New versions of products such as SQL Server have features that may become useful to the business. Upgrading before they are needed means the IT department can support business change rather than being a brake on it. This means being able to exploit the right time to market. This means growth to the business.

If a cost/benefit analysis focusses on the downside of upgrading, then the organisation risks being bypassed by its competitors.