Help Needed - Building a complete portable rig for $300!

Well... I'll try:

1. Sandisk Sansa Clip+ 8GB (Review) ~58$

Because u definitely want a small and sturdy player when jogging/biking/whatever. Sandisk makes regular FW updates, which is a huge plus, IMHO. You get your FLAC support and in the near future you'll probably get rockbox support, too.

2. 16GB microSDHC Card ~27$

For this huge FLAC collection of yours...

3. Sennheiser PX-100 II (~70$) or Koss Porta Pro (~30$)

Why those crappy semi-open headphones, you're probably asking yourself right now?!

No closed back headphones because...

1. You're sweating while biking/jogging and nothing is more irritating than a pair of sweat-soaked headphones ... and the air can't circulate around your ears with CB phones.
2. In general, they're quite heavy.

No noise canceling headphones because...

1. In addition to all those disadvantages of CB headphones, NC headphones are even heavier because of the NC electronic + battery.

No IEMs because...

1. They're tiny and light and you don't sweat that much, right. But you hear your own heartbeat and footfall sound and the sound of the cord which is rubbing against your shirt...
2. Their isolation is too good so you won't hear anything from your surroundings - I don't think that'd be very smart when biking.

Long story short: Yes, those two are crappy semi-open phones, but they're light and you can wash or replace the cushions as often as you want. But, most importantly, you can hear a bit of your surroundings while biking...

4. You won't need an amplifier ... :)

just my 2 cents.

regards.

bearmann

I have 4th gen iPod => iBasso CB-05 LOD => PA2V2 => Porta-Pro's and am very happy with the results.

Had a pair of PX-100 (first gen) and found the sound to be accurate and enjoyable. The construction is not as durable as the Koss and the Porta-Pro added bass is desirable to me while out-and-about. Lifetime Koss warranty a big + as well. Senns broke soon after giving to 16 yr old.

I agree with bearmann... and then you $ left over for whatever.

I'd go Sennheiser HD 25 -1 II headphones coupled with the humble Clip+ and possibly a microSD card.

Forget amps for the price budget you have and look to spend the most on better headphones and not players (or amps).

If you get an amp later a simple rugged small camera bag can hold your gear nicely. Most can be worn on belt or carried with shoulder strap. I have good results with the Mountainsmith brand and get them for <$10.

I recommend looking here. It has many high rated over ear headphones, but make sure they are "closed". Some are open and will leak sound and allow you to here outside noise. Also check  here.  Noise canceling is usually not recommended for various reasons... but if you really want some noise cancelling phones look here.  

Yeah noise canceling is fail. It kills the sound. Just get headphones with good isolation.

Player: Nationite S:Flo2 for killer sound quality ($150) or if you believe less is more, Sansa Clip+ ($60)

Audio Technica ATH-M50 ($100) for the best bang for your buck over-the-ear headphones, the V-Jays ($60?) for a great sounding and light, portable open headphone or in-ears for even more isolation like a pair of Fischer Audio Eterna ($70), Hippo VB ($80), Panasonic HJE900 ($100?) or Fischer Audio DBA-02 ($150?).

Best sounding combo would be the S:Flo2 from MP4nation.net combined with the DBA-02 from Bugden/Ebay/Russian vendors. 

Great sound doesn't have to kill the bank. :) 

I would go with a reliable, established DAP producer rather than the latest FOTM "look at me aren't I original?" player.

A Sansa Clip (or Clip +) will do everything you need, has a clean hp-out that is as good as lineout, is small enough to make an amp a portable option if you want that, light and has superb sound.

If you want a larger player I would go for a Cowon, a Samsung, Sony or another well-established brand.

If you don't care about file/folder browsing, MSC file transfer, any kind of usable sound customisation or any useful features really besides lineout, then an ipod isn't a bad option as there are so many accessories aimed at it.

If you want an amp, the most portable one I have heard of, and is universally well-regarded is the Arrow 12HE - very slim and loaded with unique features at a great price. There are plenty of other good portable amps (I personally have a Pico which I'm very happy with) but depending on the size of your pockets, portable sometimes stretches the definition a bit…

Headphones is so down to preference there is no point laying down a recommendation and it’s probably better to start a whole new thread on that being very specific about your needs.

Just do some research (you can use those links I provided to start) and figure out what kind of headphones you want. Then come back and ask "I want this kind of headphone .... what's the best deal?" or something like that.

You're always saying that you want a "nice" pair of headphones... what's more important for you: sound or style? (real question)

My "ultimate portable player" -

8gig ipod touch + Rhapsody subscription ($10/month) + Portapros/Melec M6/Ety ER4S depending on need. 

The ability to stream music over wifi / download at will to my ipod trumps everything else.  I absolutely love finding free time at campus and browsing unfamiliar music via charts and radio, and then being able to download full cds or whatever I want for my drive home is just great.

I have the Clip+, and can't say it sounds any better than my ipod (even streaming rhapsody), in fact I think the ipod sounds better.  The clip+ is great for gym/running due to it's 1/4 size of the ipod and cheap price, but in my (admittedly strong opinion) - no other portable player beats ipod touch + the millions of songs instantly available on rhapsody.