I hate you for asking me this because it is such an emotional issue for me. I've been asking myself the same question for over a year now. The answer has almost always been savings. I have a wife/house/car/loans and need at least $3000/month. The good thing is that I see the light at the end of the tunnel. July 2009, I thought I'd start in Feb 2010. Feb 2010, I thought I'd start in July 2010. Right now I'm aiming for next month. I know it's a moving target but it is getting really really close. If magic-pixie-unicorn-fairy gave me $6k no-strings-attached, I'd do it today. Otherwise I think by mid-Sep, I'll be in a good position to dive right in. Counting days at this point...