Job offer from a local O/O

I wouldn't call myself a new driver, but compared to some of you guys I might be. I was OTR for a while then local heavy haul flatbed driver for 3 years, till the lay off then company closure. I've been a full time student at a local College for the past 1.5 years. We are now in a situation that calls for me to go back OTR so my wife can finish her last 3 quarters of college.
Now I have a pretty sweet offer from a local O/O. I would be driving a nice truck, no touch freight, have a three state driving radius, great pay. The load will be a reefer unit filled with Kroger products to be taken to the stores in Ohio, West Virginia, and Michigan. I'd go anywhere from one to three stops and back to Columbus every night empty. Since my pay is based on a percentage after fuel, I wouldn't want to make the 1.5 hour trip home every night. So even though I could be home every night, I probably won't be.
Now the bad: He offers insurance but its $90 a week for my family! Being a married father of 3, that's a big deal. He also doesn't hold out any taxes, I'd be responsible for that. Those are my concerns. I like the thought of having a dedicated route and guaranteed home time.

I do have other offers from other companies, however I'm not able to go back out till after my finals this quarter, which is the first week in December. So I have a window to pick and choose, but id like to nail it down ASAP.

 

He has 10 trucks, and I did get the chance to talk to one of his drives who's been there for 3 years and he's happy. He says I will get the 1099 at the end of the year.
With my experience, and the fact that Im a hop,skip, and a jump from my degree (my head works , somewhat) he's agreed to pay me 40% after fuel. This is why I said I can be home every night but probable wont.

My biggest determing factor right now is finding out the amount of taxs I have to take out. People keep telling me 30%, and if its true I need to step away, and take a nap on it.