would you owner operate green if you could

Hello all,
I am seriously considering leaving my current job and buying my own truck. I have been on tugboats since I have been 17. Have been a boat captain for 8 years, and every day spent out here makes me hate the industry that much more. I use to love it out here, now I dread packing my bags for another trip.
I am seriously considering buying a truck and hitting the road. I know what it's like to be gone from the wife, I leave her at home for 30 days at a time now. I know what it's like to miss birthdays and holidays, I haven't seen Christmas in 5 years, and haven't been home for my child's first 3 birthdays. It's not being gone that I hate with the tug boat industry but the idiots that I have to constantly work with.
With all that being said, would you start green as an owner operator? If I make a career move, no way will I go back to a big company and have the same b.s to deal with day in and out.
Looking at buying a used truck, pre- 2006. Good idea or bad idea?
looking at Pulling flatbeds. When the oil field is pumping in the Gulf south ( it isn't right now) I could stay close to home, but I'm not scared of long trips.
The wife wants to ride along. Is this a good idea or not?
How hard is it to find loads starting out? Is being a new driver going to keep me from getting loads?
Any other advice for a green driver that wants to buy his own?
When I say buy, I mean pay for. I don't plan on financing. I already paid off my house, and have no other bills. If I buy the truck out right is the insurance cheaper?

Thanks for any advice in advace.

 

I have been thinking on this for 3 years. Have been saving money to buy a truck for 2. In the last 3 years I have worked at 3 different boat companies thinking I will find the right company and will be happy agian, it has yet to happen. I think 3 years ago it was an emotional decision. Now it is either going to happen or I'm going to start digging ditches. My sanity depends on it.

 

Not yet, but I will now. Thanks

 

Pre 2003 is fine with me. I do not need new things and fancy gadgets to be happy.
There is a driving school 10 minutes from my house "costal truck driving" that I plan to attend. Also my farther is a retired o/o that says he will ride along the first trip or 3 to try to help me learn the ropes.
I am going to try to get my own authority. Haven't been able to get an insurance quote with out actually owing the truck yet.