I've been a remote person for a little while now and a big advocate for it. I've thought a lot about what's hard for me, but, I'd love to hear the other side of it. What's hard about managing a remote person?
I manage and work on a small team of 4 people. Myself and one other are remote, I am at a 13 hour time difference from all of them(!) The hardest part for me is knowing what's going on during their normal workday. Something can come up that de-rails their whole day and I'm not there to be their buffer or to help prioritize. So I guess the hardest part for me, isn't my employees, it's the other employees in the company that distract them or take up their time.
We are keeping person in the office at least half a year (6 payrolls). During this time they are trained and you can understand if she/he/it fit your company. After that period we can give remote login only.