Moving dilemma (pre-warning, lengthy explanation)?

How big are the cars? Depending on what you have, you could consider renting a trailer that you can use to tow one of the two cars rather than driving both. When my company asked me to move from Virginia to Florida several years, they wanted me to drive a U-Haul truck down with some office furniture and other supplies. I towed my car down on that trip and it worked out well.