Contemplating a change in direction

My job completely sucks ass - the only redeeming thing about it is my co-workers (and last week, one of them damn near got on my last nerve - I don't do well with people who take it out on everyone around them when they have a bad day). The more I think about it, the more I'm really considering medical transcription. If I were able to do that, I'd also have the opportunity to get into other things that interest me as sidelines - candlemaking, calligraphy, piano tuning, all things I could make a little money at. I'm trying to think of pros and cons to working from home/doing freelance work. Pros: I'd save a ton on gas and parking costs; I'd be here when J left for school and when he got home; I'd be a lot less stressed; I'd have a job I could actually kick ass at. Cons: I'd have to pay for my own health insurance (mine and J's); no retirement plan except what I managed to put aside, most likely; the temptation to do stuff around the house rather than work. But then I think, hell, I've worried about benefits and retirement and insurance and salary, and look where it's gotten me - nowhere fast. Am I more likely to do better (and thus ultimately make more) doing something I enjoy, even if it's not a typical corporate-America-with-benefits position? I'm thinking yes. I just wish I knew there was a safety net there before I took the leap of faith.