09+ gets the bluetooth connectivity. (even though it kinda sucks)
Are you solely getting an 08+ for the TR6060?
If you're getting a high mileage Vette, be cautious of some of the sensors, they tend to go out a lot (The oil pressure sensor behind the intake manifold failed on both my old vettes [01 Z06, 08 Z06]).
Use the "ranger technique" for flushing your clutch master cylinder, replacing the slave cylinder isn't cheap/fun and will leak/get air when neglected.
I'd say the valve drops are about as common as the E46/92 M3 bearings and W204 C63 headbolts. But if you're too concerned over it, I probably wouldn't recommend a Z06.
I got my heads/cams/exhaust on day one, so I wouldn't know about my old one.
Here's pictures when I was at Corvette Invasion 2018.