At first I was puzzled why Tesla wanted to retrofit their already-sold cars with better batteries... beyond simply being nice to initial customers who in part, were critical to get the company going. (The downside being, there are only 2,600 Roadsters and it would be an expensive upgrade, since you can't use the normal factory lines etc. and profits would not come via the advantages of mass-production.)
However, it is clear now that the new battery has a new, denser chemical formula/composition, allowing more kWh in the same space. (or making the battery smaller/lower with the benefits mentioned above)
So now it is obvious why they are doing it... they want to get test data on the new denser battery composition before rolling it out to the other mass-produced platforms. With only 2,600 cars to update, and not all owners lining up in one clump, Tesla can take their time rolling out the new batteries, and place orders for component materials in small "custom" quantities, to ensure highest quality of battery construction, testing, process control and so on.
One more reason why Tesla leads the industry in electric cars.
It's possible those original 2,600 Roadsters will be regular recipients of new technology revisions in years to come!!! Essentially, owners getting special thanks for their early participation, by being early recipients of the latest stuff.
I am not saying Roadster owners will be used as guinea pigs, and exposed to experimental technology that may not be completely finished. What I'm saying is, the Gen2/Gen3 production numbers are hundreds of times larger than the Roadster production run, and Tesla wants to be a brand synonymous with engineering reliability and excellence; nobody can afford to pass up the benefit of all that in-the-field performance data.
While I'm here... I'm not convinced that the new batteries will remain incompatible with Superchargers. Even if the Roadster is uncomfortable to drive for long distances, Superchargers are a great resource to be able to take advantage of, if you're near one.