Keep in mind that if you pay someone more than $600 per calendar year, the IRS has pretty strict guidelines about making sure you issue a 1099. Of course, that means the assistant has to pay taxes on the earned income, which dents his bottom line. So you can always make the choice to pay an assistant under the table. What you do is up to you, but let me repeat: Always keep in mind what tax laws dictate, and make smart choices based on that.
I doubt many companies like or prefer that employees work from home. We allow the policy in order to be able to attract employees who would otherwise go elsewhere. We are heavy users of Slack, Confluence and other collaboration tools that make working at home more productive, but they cannot replace the serendipitous interactions that occur while hanging out by the nitro-coffee keg. - Manuel Vellon, Level 11