If your compressor is not engaging, then more than likely you are low our out of freon. There is a High/Low pressure switch that keeps it from engaging. If you add a can of refrigerant, your compressor should cycle on. After 1 can of freon, I would then spray down all the line connections with soapy water to look for bubbles. You could have an O-ring leaking at one of the connections. The O-rings are found at the firewall transition (passenger side), on top of the dryer (driver's front side), both sides of the condenser (behind grill both sides) and a gasket on top of the compressor. Anyway, that's the ones I change out. Haven't had to deal with the evaporator yet (under and behind glove box).
If you find a leak, then I would replace the O-ring(s), change the dryer, and pull a vacuum on it. Make sure your vacuum gauge holds at around 28 psi for an hour or so. If not you still have a leak.
You can jump a 12 volt wire to the AC clutch wire (the one with the plastic connector) temporarily to just test the clutch engagement. If you do so with the engine not running, you can then turn the compressor pulley by hand to make sure your compressor isn't locked up.
BTW, there is no reason for you to have to jump the clutch to make everything work again.