New student trucker looking for advice

I'm a 31 year old married father of three daughters under the age of 7, with another child due in April, 2014. I started truck driving school at a private school here in the Chicago area where we live last week on a part-time basis. It's been a great set up for my family. If everything goes well I should be graduating with my Illinois CDL at the end of December. I'm also currently still employed, which is why I went part-time at the school. Because of my current employment providing housing as part of my salary package, I'll have to move my family around the 1st of the year when I start with a new trucking company. Because of the lifestyle change that will come with a trucking career my wife and I have decided to move our family back to the Grand Rapids, MI area near her parents so she has a good support network when I start hitting the road. So, on top of trying to figure out everything that goes with a new career in trucking, we have a few major family events to work through over the next few months. With my given situation, I have these questions about trucking I'm seeking advice about:

1. Given my situation, what sorts of trucking companies should I be looking to apply with who would give me the best combination of good pay and home time? My wife and I are fully aware that the best pay most likely will be with OTR companies, so we are prepared and willing to have me go OTR. We just don't know what company to go with. My school has given me info on a number of companies, so far we have a short list of five companies we are looking at: Werner, US Express, Maverick, Stevens Transport and Schneider. Any advice with these would be helpful.
2. I've heard there are pay differences between dry van companies and flatbed companies. That flatbeds pay better, but have less freight. Flatbeds interest me because of the physical work that goes along with that style of trailer, I've heard it's a way to stay in shape on the road.
3. How easy is it to transfer a CDL from Illinois to Michigan when you get right out of school and are starting with new company?

Finally, if you were in my situation and starting out in trucking with a family situation like mine, what would you be looking for in a company? What sort of questions should I be asking requiters? I know there is no perfect company, just the right fit for each person and situation, and I guess that's what I'm looking for. I'm willing to put in the time and work for a company for the long haul, I want to make good money upfront at the start of my career so I can get my family out of debt soon and then move into more dedicated, regional or local work once my kids get older. Any advice would be really appreciated.