Koss PortaPros are indeed outstanding value. However, in my experience they do not benefit from amping, and can even sound worse that way. This can be good or bad, depending on whether you are looking to see what the fuss about amps is all about, or if you would rather keep things as simple as possible.
The ATH-M50 is another pair of headphones with great value. They have even lower impedance than the PortaPros, meaning they are just as easy to drive without an amp. But the M50 will benefit from amping. These are closed headphones, which are good for blocking out outside noise and stopping your music from leaking out (e.g. like in a library situation). They also fold up for transportation like the Koss ones. ~$100
ATH-AD700 is yet another bang for buck pair of headphones. Have not heard this one myself, but it has a reputation of having a nice soundstage and treble, but being lacking in the bass. cMoy Bass Boost you mentioned can fix that. Open headphones. Not the most portable, but great for FPS gaming. ~$88
If in-ear type of phones are an option for you, the Head-direct RE0 is a good choice too. And again, cMoy BB will be a good pairing in this case. ~$79
FiiO E1 is a headphone amp + Line out cable + iPod remote control all merged into one package. Quite inexpensive too. The amp draws its power from the iPod itself, so no extra batteries needed. Brilliant, in my opinion. Not head and shoulders improvement in sound over the iPod alone, but fully worth the price. Only works with Apple iPods/iPhones. Cable is kind of long, but there are ways to deal with that.. ~$20
At the entry level, don't buy an amp that costs much more than your headphones unless you intend to upgrade your headphones in the foreseeable future. Same with iMod. I don't think it would be worthwhile to pay for that unless you have a good amp and headphones already to be able to hear the improvements.
192kbps AAC/MP3 is fine for portable use. Chances are you won't be able to tell the difference between MP3 and CD quality unless you are actively listening for differences, and are familiar with the song being played, and are using higher end equipment in a quiet environment. Keep your music collection as it is, but opt for higher bitrate / lossless when getting new music. Then compare the lossless against MP3 yourself each time you upgrade your headphones. (And you will upgrade them if you hang out on head-fi, lol.) Only when you find that the MP3s sound bad should you replace them.
Quote:
Originally Posted by
REDH0RN 
Thanks for the insight. I am kinda stuck with my current audio files for a while. Whole CD collection is stored in another state. I am almost positive I used 192kbs AAC which is a couple or few clicks above the 128 standard. My whole project has to be done on the cheap. For one my TiBook and it's 40GB drive will not allow larger files in it's current state. As far as headphones I am leaning toward the Koss Porta Pro's since they are purported to be an outstanding value. My main goal now is to have great portable sound for traveling and out-and-about. I have a pair of HD595's also in storage that will demand a solid desktop amp later. The JDS Labs Bass Boost cMoy v2.02 Headphone Amplifier seems like it would serve my purposes. With the boost circuit it should be a little more versatile than other low cost amps. I am however still in the amp and phones selection process. So many choices...