In a way, I had thought of this as a work + lifestyle experiment.
Thanks everyone for your feedback. I didn't think people were still discussing this, but I was glad to see there has been much more said since I last looked at it. Overall, I think most people would suggest not doing this, but at the same time, do what is right for you.
It's still not 100% certain, but the company I'm contracting with would like to see this happen, and my employer is looking into funding my days off the trail, the shipping costs of the laptop, and a purchase of a new laptop. I've taken map man's
Southbound AT Hiking Rates, the AT Thru-Hiker's Companion, and my own personal physical condition and drive and created a day-by-day breakdown of my hike, with me finishing in 134 days (about two days faster than the average) on 11/15/2013. This included no zero-days, but enough town days with minimum miles. My next step is to find an estimated date and the town and establishment of my work days. I decided to break the 30 days into four 5-day stays and five 2-day stays. I would do my best to spread these evenly out the hike, avoiding as many weekends as possible, and avoiding towns where the cheapest stay is $150/day. I'd like to average $100/day in rest and food. Also, I would contact the establishment where I would be working before I start my hike to confirm with them my plans and their abilities to provide an environment where i can work.
The thing that worries me the most is missing out on building strong friendships; however, this was not a goal of mine when I decided to do the AT. Not only did I choose Southbound for the more convenient date, but I wanted more solitude and to be able to push myself at my own pace. I imagine I'd still make friends, but maybe not "best" friends. Otherwise, I love this new job I have. The team is great, the boss is awesome, and I get to work with Google Maps, weather data, and trail data. When they took me on for a three month contract they asked about a contract-to-hire, but I turned them down because I knew I was walking the AT. It seems they really would like me to stick around, as would I, so this would continue our relationship. Also, I like to hike; I like being connected with mother nature, I like being minimalist, and I like the physical conditioning. But, I do get bored. Maybe working with technologies I enjoy every two to three weeks will be a good break.
Another concern of mine was extending the trip in December, where I imagine it will be colder and involve more snow.