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+1 on the broken oil filler tube (especially if the oil is on the OUTSIDE of the intake manifold). Imagine an oil leak which only manifests itself when you brake hard and turn left hard. And then gets worse when you try to put more oil in the engine!
Try putting a voltmeter on the battery. With the engine off, it should read somewhere above 12 volts. When you first start the engine, it should jump up to about 14 volts, and then gradually (over about 15-20 minutes) the voltage will go down slightly. If it doesn't do these things, try replacing the voltage regulator on the alternator. Much cheaper than a new alternator...
Might also want to check that the water pump, alternator, P/S pump, or A/C compressor have not seized. Seized accessory unit can be one reason for V-belt failure...
It sounds to me like the front engine mount. You cannot see whether it's damaged without removing one of the rear splash covers on the bottom of the car, and perhaps even undoing a couple of the nuts and removing one of the mounts rubber/polyurethane side plate. The hard shifting you refer to is only a symptom for manual transmission cars...
Am I the only one who notices the elephant in the room? If you use narrower wheels, you will lose lateral grip, either by shoehorning the stock tires on narrower rims, or by going down in tire width... To finish the answer to your question, your (986?) Boxster S came stock with 205/50-17 tires on 7x17ET55 wheels on the front, and 255/40-17 tires on 8.5x17ET50 wheels on the rear. The Cayman wheels you're looking at are 6.5x17ET55 on the front and 8x17ET40 on the rear. If you're still using 205/50-17 tires on the front, they will fit the Cayman wheels, and since they are the same offset, you will not need spacers to use these wheels. For the rear, 8 inch rims are 1/2 inch narrower than the spec for 255/40-17 tires, but you can probably get them to fit (you will effect the handling of the rear by doing this). Since the Cayman wheels have 10mm less offset, they will stick out 10mm more (which should not be an issue; some people put 10" wheels and 285 tires with around 40mm offset on 986's), so you will not need spacers for the rear wheels either. It is worth noting that the latest Boxsters and Caymans have gone back to 7x17 fronts and 8.5x17 rears as their standard wheel size...