Here's a slightly different scenario, and I have no idea how to direct this person.

An accountant has asked me how he can move into the cloud. He's interested in moving out of his centralized office and wants to be able to work from home and have his assistant and an occasional partner all able to work from where they are.

The biggest challenge here, IMO, is that he has several unique situations. First, the way he handles things is to have companies send him their Quickbooks company files. This means he ends up with files made in different versions of Quickbooks. He can't open these files in his latest version of the program because then he couldn't send it back to the client who wouldn't be able to open it anymore.

I have no idea how to get around this and let him work from home. He couldn't just use Quickbooks online. Is there a way he could access this on a server in a virtual machine or something? And then have another user log in to another VM and also use any of these applications? I don't know if this would work...