I've been tutoring for 26 years, and in addition have always been very tech savvy. At the beginning of online tutoring, perhaps 10 years or so ago, I used to 'tutor via email' - yes, via email! I would arrange a time to be online, and the tutee and I would go back and forth for 1 hour with 'live' email. Surprisingly, not least of all because at the time the expectations were entirely different than they are now, it worked OK.
As technology changed I went through some difficult transitions. A LOT of technology came and went, and I found it increasingly frustrating. It never seemed to work well, the connections were often plagued by issues, and the whole thing was a massive stop/start process - all very aggravating and dissatisfying to me and the students. Things didn't change for me until about four years ago. The combination of my Mac Book Pro, my iPad, Skype and Doceri software basically solved the problem. Here's how it works.
I call the student via Skype on my Mac, and almost immediately turn off the video (this helps with the connection and we really don't need to see one another). Then I share my screen with them via the Skype feature that allows that. In the meantime, I fire up the Doceri software on my Mac, and connect my iPad to it via WiFi. Then I have a clear audio connection, and a tablet that I can write on, share (including documents) with the tutee and we generally have a great exchange. If kids need to show me work they can turn ON the video link, email to me, or take pictures and text etc. I works really, really well. FINALLY, a critical mass of online tutoring happiness was reached!
When I initially figured all of this out, I used it with kids that I tutored in remote locations all over the USA, and across the world. While I was doing that, I continued with my face-to-face work here in Atlanta. Remote tutoring is NOT for everyone, so it worked well for kids that preferred one method over another. HOWEVER, I have found that the flexibility that online offers, AND the fact that so many kids are now increasingly comfortable with the remote situation, that many kids who I could reach locally, are keen to try the online route first.