I've been at my current employer for just about 2 weeks shy of 1 year. At first, I was in the office 5 days per week but as winter rolled around many of us started working from home with the bad weather. Spring and summer came and most of us kept with the new-found perk of working from home. Most of my team usually only goes into the office once, maybe twice per week.
We usually just go in just for the sake of physically seeing each other, or if we have a meeting to attend. The latter is less important because our actual boss, and more senior half of our team works in a completely different state. So any meetings we have are just updates about our building, or status reports to a general manager for our department but this person is in no way responsible for delegating tasks to us or anything.
Lately, I've been growing less content with where I live in regards to the particular region and quite frankly I miss all my old friends and family. Moving here was sort of a "social experiment" to try and move away from home and what not. So, how can I bring this up with my employer?
For what it's worth, I'm a contract employee (most of us are, actually) on a rolling 6-month contract and I recently just got another extension. My actual boss has let me travel home for a week on two separate occasions to work remotely, already.
TL;DR I work from home 3 or 4 days per week and have no significant reason to go into the office. How can I, as a contract employee, try to discuss the option of permanently working remotely and moving ~500 miles back home?