Sold my old rig and starting over -- Need advice!

You asked for opinions so I hope I don't offend you with mine. I would keep the van so your wife can economically shuttle the kids. At approx. $234,000 without college to raise a child to age 17, I would call my family "complete" and nix the fourth child.(That's the part that I was worried about) ;)...sorry. Then I would buy a 2500 truck so you can tow a big enough trailer to make 5 of you comfortable. JMO. Whatever way you go buy enough tow vehicle so you are all safe!