Towing Advice

I'm soon to be heading out towing/racing again, with a longer than ever had before rig and trailer at almost 60' long. I've driven semi's before, longer that that, but that's another story. Yes, bumper pull. I intend to have my driveway widened even, due to the fact we'll be entering on a right hand turn, (gotta see it to understand I guess). Any suggestions other than I hire a driver?