In the days when we learned our stuff from the likes of Amiga Format and CUAmiga, we were advised to limit overclocking any 68-series CPU to 15% of its stated speed. That means any standard 50MHz chip shouldn't be pushed beyond 58MHz or so. Having said that, plenty of people have upped their 060 to 66MHz and beyond. I've read of them running at 80MHz or so, but how long they lasted is another issue. Running a CPU above its design spec will reduce its lifespan, but individual chips vary.
I run my Apollo 1260 at 64MHz (the fastest oscillator Maplins sold) and never had a problem with it in ten years. It is however, in a tower case which will make a difference. The standard A1200 case is pretty restricted and though the 060s run relatively cool, upping it to 66MHz will introduce a need for more air. I once fitted a standard 030/50 in my desktop and that would heat crash when running Imagine renders. Jacking up the case and leaving the trapdoor off solved it. A fan also helped but it was very loud.
To a large extent it may depend on what you use it for. My tower has a heat sink on the CPU but no fan, it wasn't necessary and was noisey. Don't know if an 060/66 runs cooler than an 030/50, but I'm sure someone here will tell us.
My advice is go ahead and have fun.
JaX