A little late in responding to this one.
I love the idea of an HSA for training. I have have an HSA for medical expenses and it is a great option.
The problem with the HSA for training idea is that it is company funded and therefore company controlled. The HSA for medical expenses is funded by me and controlled by me (within a set of rules).
I go through the budget process every year, just to be told I can't actually use the moneys that were budgeted for software. training. etc. when I ask for them. So much like our state government, the fund may be allocated by the company for one thing but without a lock box around it too many hands will use it for whatever they want.