To answer your questions more directly............
And I want to play consistently at 500 watts. How much headroom should I plan on having so I don't overwork my amp?
An amplifier rated at 500 watts RMS will put out 500 watts continuously, but you have to allow for the transient peaks that we all have in our playing. Some folks play a lot more cleanly and evenly than others, so it all depends on your playing; even the best player will have transients of 6db, some will have 9db or 12db spikes. If you really wanted to put out 500 watts continuous, and do it cleanly without loads of compression, you'd need 2000 watts IF you can hold your transients to 6db or less; more likely, you'd need 4000 or so to have enough headroom to put out 500 watts continuous while allowing for 9db transients.
plus how much slack (in terms of watts) should I give my speaker cabinet considering that I'll be running at 500 watts.
As long as the manufacturer isn't fudging the RMS rating, a speaker rated at 500 watts will actually handle 500 watts continuous. BUT you really have to see how they come by that rating. A lot of times it's at a fairly high frequency, so if you hit it with 500 watts at 41Hz it'll cry uncle in a big way.
All of this stuff
can be broken down and measured, and specific conclusions can be had, but it takes a good bit of electronic gear to come up with absolute data.
That's why you really have to use some general guidelines, and then use your ears for the rest. Learn the sound of a power amp clipping, and learn the sound of a speaker distorting from being driven too hard. If your power amp is clipping but your speakers are clean, you can run more wattage. If your power amp is clean but your speakers are distorting, you need more speaker capacity.
You basically use the rule of having a power amp puts out 2x your speakers rating. If that isn't loud enough, you need more power AND more speaker capacity.
There are other ways to boost volume, mainly by increasing the efficiency of your speaker system by using multiple drivers, but keeping your available power and speaker capacity properly matched will get you the most volume from the smallest rig.