When you click on links to various merchants on this site and make a purchase, this can result in this site earning a commission. Affiliate programs and affiliations include, but are not limited to, the eBay Partner Network.
I had two C5s, a 97 that I purchased new and a 2003 Z06 that I purchased used. Both were great cars. The downsides of those cars were the seats. They were terrible. The seat bottom foam will be cut by the seat springs and will sink down around the springs requiring installation of an aftermarket kit to get your butt off the seat mechanism. The seats have no lateral support and you sway from side to side when going around corners. Same, goes for the C6 cars. As for wrenching on the cars there is little difference if any between wrenching on a C5, C6 or C7. They need little engine work unless somebody has damaged them. Spark Plugs are good for 100K miles on all of them. They require different but similar scanning tools. An OBD2 scanner won't cut it on any of them. Brake maintenance is brake maintenance no matter the car so there is nothing special there. Transmissions are very similar especially the M6 and M7 or the A4 in the C5 and the A6 in the C6 and 2014 C7.
However, the C7 is a much more comfortable car to drive and ride in. It is better looking and even though I have had mine for 8 plus years it still gets plenty of thumbs up from pedestrians.