Take a look at all those hip Ruby frameworks and look at when Yehuda Katz last made a commit to Merb and you'll figure out why CIOs still buy SAP and pay for Oracle. IBM is lucky not to deal with the 'hip and trendy' demographic- it'd just further damage their already faltering image in the corporate world.
The real market share they should be trying to pickup is not the frivolous Web 3.0ish junk. They instead should be pushing out a POWER8 + DB2 + fault-tolerant (i.e., milliseconds failover, not seconds) for under 250k with an ERP attached to it (partner with SAP Business One, 98% of the businesses doing under 250MM in gross per annum don't need more htan that). AIX 7 already has "Cluster-aware" software that does this, they just need to include it by default for up to 4U. THEN, start price gouging. Market it under the name "NEVER/down", partner with PureStorage or one of the new "EMC-killers", and aggressively market it like they did during the Watson hype (tennis ad-buys, advertising at LeMons, etc).
Spoken like someone who has never tried picking up code that worked fine on WAS 6.1 and tried running it on 8.5.
You're right though - moving up major releases can break things sometimes. I spent another couple of months forward-porting to Liberty so they could run 8.x but honestly most of the breaks I dealt with was dealing with third-party functionality that the old off-shore team decided to throw in. Regardless, during that period of time, my clients business was fully operational on that new hardware with a secure, seamless transition.
I guess you sort of get the same 'future proofing' these days with VMware (the analog is basically: having old hardware, then buying new hardware and vMotioning your production instance to the new VMware ESX cluster), but you certainly didn't have that option 15 years ago, when my client was choosing what environment to run his oil/commodities firm. And that's just support on the hardware stack, rather than the 10+ year support that most businesses want as a guarantee.
