Hello,
 
I currently have the Klipsch image S4s and I am looking to upgrade to something better but am a bit overwhelmed by all of the choices.  I listen to mostly indie rock and have been looking at the UE triple fi (which I am really leaning towards) as well as westone 2s but I am not opposed to full size headphones either as I will mostly be using these in the library while doing homework which pretty much means that I won't be going with open back headphones unless there is a huge gain over other headphones.  I am looking for recommendations for new headphones as the klipsch are aging and beginning to fall apart.  Also, I'm not sure what would be better when looking for headphones, should I be looking for BA or Dynamic drivers and does the number of them really make a big enough difference to justify the higher prices?
 
Thanks in advance

You should checkout the Hifiman RE262 ($150), the mids are awesome along with a really good soundstage.  The bass doesn't have the impact of the S4 but nothing a little EQ'ing can't fix.  I had both the TF10 and W2 which I just recently sold and the RE262 sounds better than both for music like what you listen to.  They have an impedance of 150 ohms which means you have to give them quite a bit more volume than the S4 and if you get an amp like the FiiO E6 ($25 on Amazon) they sound even better but they still sound great without.
 
Don't mean to over welm you even more but the Rockit Sound R-50 ($120), Ortofon e-Q5 ($199) are two more that sound better than the TF10 and W2 imo and would work well with indie rock or alternative.  Over all the e-Q5 is the best but if you just listen to indie rock the RE262 would probably work better plus it $50 cheaper.

I am quite fond of HiFiMan products as I I have tried some of the over the ear headphones and really liked them.  I have read reviews of the RE-262s and have heard nothing but good things, but I was also considering getting the TF10 and having them reshelled as custom molded IEMs, would this be a better option or should I just get the RE-262s?  As for an amp I was looking at the Fiio E11 connected to my ipod through the dock connector.

Here's a bunch of under $200.00 threads.
 
 
http://www.head-fi.org/t/621723/good-earphones-for-under-200
 
http://www.head-fi.org/t/626206/best-iems-in-under-200
 
http://www.head-fi.org/t/603299/under-200
 
http://www.head-fi.org/t/622595/iem-under-200
 
http://www.head-fi.org/t/612602/earbuds-under-200

Well the TF10's mids aren't the best, the TF10 really sound the best with EDM but for the music you listen to the RE262 would be perfect imo.
 
As for the amp I to have the E11 and its even better than the E6 (which I have as well) at make the RE262 shine, they some of the best mids I've heard and that's the meat of music so I think you should get the RE262 over a TF10 or reshelled TF10.

I am also open to on ear/over the ear headphones, any suggestions as to what would be the better way to go, although I'm starting to lean towards the RE-262 but would there be a big difference going from the klipsch to these, also how's the sibilance on the RE-262 as that was my biggest gripe with the klipsch.

There's a huge difference from the S4, its like going from a Honda Civic SI to a Porsche 911 and they have no sibilance and vocals sound great an the highs still have good detail.  My first decent IEM was the S4 and the RE262 is so much better that its not even close, I look at Jokers ratings where the S4 has a 6.7 in SQ and the RE262 is a 9.1 (I'd give them more like a 9.2 or 9.3 out of 10), that's a big difference.
 
I don't use over ears headphones so I can't say but the AT M-50 seems to be one of if not the best in your price range, I think good IEM's have much better over all detail than headphones at least headphones in the price range your looking at.

I have decided to buy the RE-262 and the Fiio E11 to power them, thank you so much Techno Kid as I was pretty lost in the world of options I had at my price range and you last post about them definitely gave me confidence about my choice, now I can't wait to hear the new headphones.

I tend to prefer the sound of full-size headphone over IEM. A good closed one under $200 is the HD25.
I even prefer an M50 over most if not all IEMs in the $130 range.

I was looking at the HD-25 II but was not sure, would that be noticeably better than HE-262s, I would probably still get the Fiio E11 with them to drive them.

Haven't heard the RE262 so can't comment, but headphones fundamentally provide a different listening experience to IEM, apples to oranges. 
Generally it's a bigger sound than comparable IEM, though some really good IEM can be more accurate or tuned better. I personally will take the bigger sound, and I'm sure a lot of people (but not all) think the same.

Well the RE262 actually have a large headphone like soundstage and are more accurate than headphones in the same price range imo.  That's why I prefer IEM's over headphone because I feel you get better over all detail and accuracy though I haven't heard any headphones like the HD800 or LCD-2 which I'm sure have amazing detail and accuracy but they cost over $1000.
 
Where did you find a pair of HD-25's under $200 or are they used ones from the For Sale forum?  I still think after reading jokers review of the HD-25 that the RE262 has better detailing but since I haven't heard the HD-25 I can't say for sure.
 
If you looking to go over $200 I suggest taking a good look at the e-Q5, they have a little bit more micro detail over the RE262 but not by much with more bass impact and depth and a soundstage thats just as large.  When I got mine I started to sale a lot of my other IEM's since I know I wasn't going to listen to them much anymore.  I'm really not trying to sound like a fanboy (but I know I am) its just I really think the sound great and at just under $200 (a $1 under) are well worth it imo.
 
OK I promise I'm done suggesting IEM's now, but really get the RE262 or e-Q5 

The HD25 is $199 at Amazon atm.
 
IEM is detailed for sure, but with headphones the sound is more 'felt' rather than 'heard', this is a more natural experience for me. With IEMs, incl. the e-Q5 I've never felt the sensation of being 'there'. I always know the sound is coming from an IEM. Headphones will never be quite as good as speakers int hat sense, but it is a step towards that. This topic has been beaten to death, but I guess another point of view will be good for the OP. Anyway HD25 is a very good portable headphone sub-$200, if the OP wants to go toward that direction.
 
Another good thing about IEMs is that there are a lot more choices; therefore, it's easier to get closer toward one's sound sig preference. But that point is kind of moot when you are starting the hobby and just want to buy one cans.

It sure is, that's a good deal but one thing that might make the RE262 or e-Q5 better is that the HD-25 actually has a rather small soundstage for a headphone as joker stated in his review.  For me that's a deal breaker but for the OP that may not be a problem because they do seem to be one of the best on-ear headphones under $400 or $500.

A small soundstage from a full-size is still plenty spacious, but yes immersion can be an issue with the hd25, though other good things about the sound compensate for it.
Anyway it's more of a shout-out to full-size headphones in general rather than just the hd25, there are plenty closed variety that is very good at this price range.