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How can I tell what the biggest amp I can use? I have a set of CDT ES-520's, with a JL 300/2 hooked up. Would there be a bennefit of going with more watts? Like 500/2?
maybe, but at cost. They are rated at 160 watts rms and your current amp is 150 watts rms. This 600 watt max rating is a bunch of crap. 150 watts rms to a 5.25" speaker is a lot. Going to a 250 watt rms amp will maybe get you 2 db more output but it will also decease the life of the speakers. Those speakers are not cheap either. IMO, do not do it.
Now if this question was for a subwoofer, the answer would be different
Some people are very big believers in "headroom" which is the amount of total watts that the amp has available for large transients in music (big changes .. think like large orchestral peaks etc). The actual watts that your speakers are seeing during normal listening is probably far smaller than you think it is even with 150 watts "available" to use it is likely only using 35-60 watts during normal use (maybe even less). This "headroom" thing most people feel is that even though you have more than the advertised safe watts for a given speaker you should be ok because the amp is less likely to send a clipped signal or distorted watts during those large transients in music (especially taxing when we have it cranked up).
In general if driven in their recommended frequency range most speakers will take a fair amount of watts OVER their recommended amount as long as those watts are clean and distortion free. You can send a 500 watt sub 800 clean watts in the correct set up (crossover points, proper box etc) but you can ruin that sub with 150 distorted watts.
I guess what I am trying to say is with proper system layout and setup you could certainly run more watts if you wish to, but I do not really think it is necessary and the performance benefits may not be worth the expense (generally you get some improved midbass response from adding watts)