If you were in a position that working from home was a second income for the household, I think it would be a great thing. But in that case, everyone needs to understand that while Person X may be working form home, that doesn't mean they are there to also do all the regular daily chores as well. You coudl't spend 7 hours working on a Web Design project and still be expected to have the laundry, dishes and whatever else done at the end of the day as well.
Anyways, I'm sure I'm rambling now, and I imagine you have probably thoguht of a fair bit of this already, but I figure advice is free to give, and free to listen to ... :)
I love the tech industry, but with a thousand and 1 different web/graphic design companies out there already, I can't imagine it would be easy to be "the new guy" looking to create a name for themselves. For something like that, I think it would pay to talk to local busniesses, golf courses, sporting associations, community groups, etc.. and find out who or if they are using anyone to pofessionally design for them, or administer their websites. Local is probably going to be the easiest - and you coudl always start small if you could find a few companies willign to do business - maybe get some design contracts, and ven "maintenance" contracts for their websites. It would cut into your nights and weekends, but to do it as a part time tihing for a while and get a feel for it, and for hte availability of the work in your area woudl give you a good idea if a permanent change would even be feasible.
Not sure I can give you any real advice. I was kind of forced into working from home due to health reasons. Right now, I have a variety of "Jobs" that I do to try and make ends meet. Auto Repair, Computer Repair, Home Renovations (mostly hardwod flooring), and pretty much anything else people need done. The jobs the require me to work at the clients house are all local, which keeps me close to home in case my health changes over the course of a day.
I wish I could tell you it's a great way to live, but to be honest, I'd rather be working for someone. It's a struggle to find the work, do the work, then track down payment fo rthe work - and yuo are rarely if ever paid for the first and last phase of that circle, so the days get longer, and the money never really catches up.
Getting set up and creating a Customer Base is the hardest part. it takes time to do somethign like that, and unless a person has a "nest egg" they are willign to use to hold them overduring that time (a year is a reasonable expectation), then making the transition requires some serious commitment.
