I've never gotten this "more headroom" argument. Because if your amp can put out 1000 watts and your speakers can only really handle 500, the reality is that you don't have that headroom. Sure, your amp might be clean up to 1000 watts, but you can't actually use that much. You can only use 500.
I prefer a cab that handles enough power to not care if my amp is completely cranked. Speakers can be expensive to repair.
So here's part of the answer for the OP about the amp being able to put out more power than the speakers can handle. You almost never run your amp at maximum output because you rarely need to, especially if you have an 800 watt amp. If you run an amp that is capable of delivering more watts than the speaker can handle, your amp is going to just cruise along and easily put out whatever lower amount of watts it is you need. That means the amp runs with less heat and less heat means more reliability and less wear and tear on internal components - longer life for you amp. So that's a good thing. However it does mean that you need to pay attention to what you are hearing and if you start hearing farting sounds from your speakers, either turn your bass EQ down a couple of clicks and then drop the master if needed, or just go right to the master and drop it down. Just pay attention to what you are playing and how it sounds. Having an amp with more than enough power also makes it easier to add more cabinets if you want to.
I ran a couple of cabs off a 400 watt amp for a while. One cab had power handling of 200 watts and the other only 100-watts. If I played to aggressively - got too loud - the 100-watt cab would start to distort and I would have to back off immediately. I later replaced that 100-watt cab with a 400-watt power-handling cab and no longer needed to worry much about it. However, I could still hurt the cabs even though they were capable of handling more watts than the amp could deliver if I boosted the bass EQ too much. So you still have to pay attention to what you're playing and how you're playing it.
OK...this is the part where I tell you I now play with a cabinet that can handle more power than my amp can put out. I have an 800-watt amp and the DNS410 cab can handle 1400-watts. So I really don't need to worry much about it. Good news is that the cab is so efficient that it gets unbearably loud before I can run 800-watts into it. I'm not worried about hurting the speakers in my cab. That efficiency allows my amp to use less power for more than enough volume so I run the master typically between 9 o'clock and 9:30 , and my amp gets warm but not hot. Truth be known, I don't need an 800-watt amp to drive this cab to gig levels, but you never know when you might be asked to play a stadium...always be prepared.
Another variable that perhaps hasn't been thought about is speaker efficiency. If your speakers have high efficiency to start with, it doesn't take as much power to make them loud, so you may not need a particularly powerful amp. If on the other hand you have a speaker cab that has high power handling but it isn't efficient, then your lower-watt amp might not be able to get your speaker cab up to gig volumes. My current, high-watt handling 410 has an SPL rating of 106db 1W/1M (2.83v/1M), which is huge. The 410 it replaced had an SPL of 92 db 1W/1M (2.83v/1M), which is pretty poor. So my newer cab not only handles 3 times the watts, it's also far more efficient - 14db louder with 1 watt powering it.
So this stuff really is a balance kind of thing and there are many ways to make it work satisfactorily. If you have a cab capable of handling far more watts than your amp can put out and your amp doesn't have enough watts to drive that cab to gig volumes, then you have a problem where you should either use a more powerful amp OR more efficient speaker cabs. So there are a couple of choices for that problem.
On the other hand, if you amp can put out more than the speakers can handle, then you have to be sure to pay attention to your sound so you cam recognize and compensate for any speaker stress before it creases your speaker, melts your voice coil, or just tears the cones apart. Listening to what you're playing really isn't that hard to do.
Lots of ways to skin this cat.
