How to "Train" Your Virtual Assistant
If you hired a new employee, you'd train that person to use your systems, your equipment, any special programs you have, how to fit into your company's culture, and so much more. And you'd pay the employee while being trained.
The notion that you shouldn't have to train your VA, and/or that you shouldn't have to pay your VA while she learns is bunk. If you'd customarily pay an employee for it, you should absolutely pay your VA for it - whatever "it" is.
First of all, VAs aren't psychic. If you don't train your VA about your business, she's simply never going to know what she needs to support you fully. If you believe that, somehow, the VA and you will decide to work together, and instantly the VA will know exactly what to do, how you like things done, who to go to for certain needs, who your clients are, how you want to be represented, or any number of other things along those lines, you have unrealistic expectations and are going to be woefully disappointed in the experience of working with her.
As for paying while the VA learns, of course that's your responsibility. Why would you think otherwise? VAs bill you for 100% productive time. Part of that productive time will always be learning something for you. VA should learn for you on your dime. VAs should use software that you buyassuming it's software you need and the VA has no other current use for.
Always remember, working with a VA was never meant to be the low-cost alternative to hiring an employee. It's always been meant to be the convenient alternative. If you approach your working relationship with that in mind, you'll prevent your having to have any number of fairly uncomfortable conversations, and you won't (unwittingly or not) push your VA into a corner where she'll feel inappropriately called to make a choice between her own appropriate business standards and your unrealistic expectation of her.