Q:

What can I do to prepare for working remotely?

Background info:
I currently work on site (database developer) but will be moving to another state in a month. My boss has given me the okay to work remotely. I'll be the first remote worker in my office, and I've never worked remotely before. I've been in my position for a year, and this is my first job out of college.
We are working on getting all the equipment I need. I'm more concerned about setting up expectations. What do I need to discuss with my boss before moving to make the transition as smooth as possible and alleviate any concerns he may have? 
Here's what I've come up with so far:

Communication expectations
Working hours and availability
Overtime
Travel expectations
Reimbursement for business expenses
Time frame for reviewing the remote arrangement to make sure it's working out for me and him.

A:

I was in your boat about 8 years ago.  I decided I did not want to live in the city my company moved to, so I moved back to where it started.   They allowed me to do so.  However, the dynamic is different.
Here's a list of everything you will need to be proactive about:
1: EVERYTHING
This is the biggest thing you may not be prepared for.  If you have no physical presence, your battles are harder to win, and you will have to give way more effort to get the information you need.  In short, basically assume that nobody will go out of their way to get you the information you need.  You will have to become a squeaky wheel.  In my experience, certain things I thought needed to be done didn't get done, as I was the main advocate, and I was on the other side of the planet.
Your list is good, and communication expectations is the most important one.  It does tie in a bit with what I previously stated.  Not sure if your group has regular meetings.  If not, I highly recommend them.  If not a quick 15 minute one per day, then a longer one a couple of times a week.  
Combining availability with communication: Make sure everyone knows when you start, when you go to lunch, when you're back, and when you're done for the day.  If an issue happens and you're unavailable, it looks twice as bad as if you work in the office, but are away from your desk.  
Again, these are based on my experience.  Your mileage may vary, of course.

A:

I've been doing the same for a few years with various companies. One of the main things I've struggled with is getting connected. There's nothing wrong with my Internet access, but some companies are trying to increase their network security and remote workers get hit the hardest. Here are potential policies to be concerned with:

Must use company hardware to access network. You may have a company PC but enjoy using your laptop occasionally. You could lose that.
Two-Factor Authentication. You can use a cell phone for some of these, but there could be a connection issue or message expense. Some have a key-fob with the security numbers generated. All of this is great when it works, but if things fail, being away from the office can limit your support option. If you go a week without access, that could be a problem.
Other security issues accessing servers and databases. It could be some strange think like working with linked servers and the credentials don't carry-over.

I know these examples could all be resolved, but it could take time or hinder your ability to perform. Early on, you're going to be very paranoid that others will think you've slacked off since the move. 
Keep positive and always communicate. Pick the phone up and call more than you did at the office. You don't have as much face to face as you use to. There will be little jokes about how you're not working or sitting there in your underwear, etc. Laugh them off initially, but make sure your supervisor knows you're getting things done and as many others as possible. Don't let the haters who are back at the office take it out on you. Let them know you're setting the standard and if everyone believes this worked out, it could lead to more people working from home even if it is just a day or two a week.

A:

Be proactive about communication. Talk to people at the company on a regular basis. It's easy to assume you're not doing anything if the person you're reporting to doesn't understand what you do, and isn't getting updates. 
Make sure that these meetings actually happen. Often they'll be pushed off, forgotten, and eventually ignored. See the first point.
Also, talk to your family. When you're working, you're working. It took a very long time for my wife to get this.

