I had the hard decision between wheeled and CTL last year, went with CTL and so happy I did. It's not even close how much faster it moves dirt, and how many jobs I wouldn't be able to do with a wheeled machine. I got a 13 Deere 319 and other then a recent issue with aux hydraulics it's been perfect for the 200 hours i've put on it, at 2200 now. I did consider jumping from $30k to $40k but it was just too much money for how much I use it. It might see 400-500 hours a year so I could never justify new, but at the same time wanted someone that wasn't worn out. I changed out every single fluid when I got it, and changing the oil in the drives every 200 hours, very cheap insurance. The drives are pricey and it would suck to need one or worse yet two in a short time but at least the bright side is that is the biggest undercarriage expense and you'd be set for a long time after. Renting is a pain. If you only need a CTL for a very small portion and wheels would suffice it may be a decent idea. But for virtually everything I do tracks are superior even when it's dry they just push dirt so much faster, more stable for piles, etc.
The only thing I regret is buying a Deere for the controls, they are not good. Every time I jump back in a Case I realize just how bad they are. If i'm running it a lot I get use to it, but I still don't like them.