I made the self employment jump in March of this year. My wife works part time but doesn't qualify for insurance or benefits.
We have Conventry One and pay $559/month for a family of 3. Our deductible is $1,750, 80/20, max out of pocket is $5,000. $50 out of pocket for doctors visit. Hospital copay of $250. This includes no dental or eye insurance, we pay that out of pocket. Out dentist visit yesterday was $480 for 2 cleansing and 2 x-rays.
When I was fully employed I was paying around $20-$30 a week for insurance.
I left my full time job building power plants due to not going any where in the company and wanting to start a family. It was also a very hostile and stressful environment; lots of back stabbing. I worked there 6.5 years and my pay only went up $5k in those years to around $70k. I worked 60-80hrs a week and I was salary so no extra pay.
With that said catman, I completely understand not being happy and wanting to move on. I loved about 10% of my job. The planning, lift plans, scheduling, and coming up with new/cleaver ideas to get the work done was great. But 90% of my job was dealing with corporate requirements and dealing with coworkers and/or craft guys that didn't take it serious.
Before I quit I know I shouldn't have but my quality of life was really bad and had to leave. I've always wanted to be self employed being my Dad has started & sold many businesses and is very successful.
I'm having a very hard time making money right now and will have to get another job with an engineering firm being I could make $70k-$80k, which is better than almost nothing right now, haha.
If you've done all your researched, have everything setup, and see that work is steady then I would first do more advertising to get a larger back log and then look at making the jump.
I'd just hate to see someone start a business without being all setup like I did.
Sorry for the long response.
Yellowchevy