I'm not sure how this applies. How many businesses are running Linux workstations and need Adobe on them? Again this seems to me like a likely very small set. I don't see the absence of Adobe software in Linux as being a critical impediment to Linux migration for businesses who want to do that, either.
Well, I'd put it in a 2x2 matrix with low/high impact, low/high corporate usage. High/highs is stuff like your office suite, a lot of people use it and quite a lot. Low/high are things like time sheet recording, people need to do it but it's a very minor part of their work day. Both of these you generally need to have good solutions for since you'd be wasting so many people's time otherwise, the heavily used of course more so. Low/lows you don't really need to care much about, unless they add up to some extraordinary amounts. The killer is often the high/lows, basically the specialized tools a few in your organization use.
The (strike:problem) challenge is that these tools are different. For example, your graphics department might rely heavily on Photoshop. Nobody else in the business might care about that, but they again have their own tools they care about. Retraining, lost productivity and lower output quality can be significant costs. Existing workflows and procedures must be migrated. Forced migration may lead to employee dissatisfaction and higher turnover as they want to continue their career towards becoming a Photoshop expert. Those costs have to be considered relative to the gains of making a migration. I can do an in-depth study, if you got funding...
Seriously though, I think more plans about migrating to Linux dies from a thousand cuts rather than one fatal blow. I haven't done an OS migration but I've seen some others, the major issues are under control. It's all those minor "uh oh, we didn't think of that" issues with emergency band-aids and workarounds that tends to turn it into a fire fighting exercise.