Well there are alot of variables to consider. Good job giving your listening habits, most people dont even account for this when talking about charging system needs.
How much of that 110amps does the car use regularly? How bass heavy, and thus power hungry, is the music you listen to? How much of a voltage drop are you willing to accept on a regular basis? Does dimming lights bother you, or do you really not care that much? These are some of the variables I cannot answer, and some of which you probably cant either.
In the end I generally recommend that if its reasonably close to working, try the stock alt first and see what happens. Carry batt cables with you. //content.invisioncic.com/y282845/emoticons/wink.gif.608e3ea05f1a9f98611af0861652f8fb.gif If the system is grossly larger than the charging system should accommodate, only then do I recommend a H.O. right away.
Upgrade big 3 first. Then upgrade your batt if its old or worn. You can also consider adding a rear batt at this point, depending on your exact situation. After you have upgraded these methods, if you still need it, upgrade your alt. But as I said above, if you fork out the coin for some 5kwt amplifier, you should pretty much add the price of a H.O. on to the price tag automatically. Otherwise every time you brag about your 5kwt daily driver system, you are only fooling yourself (to nobody in particular, just saying for example).