Here is the dilemma, I lost all of my music. My small collection of 10,000 songs.
I have decided to go all FLAC and to do away with MP3s totally and move on to lossless audio.
Buy a small android tablet as my portable player with a portable amp.
 
Now what IEM's should I get?
My budget is $600 atm for a pair of IEM's and Amp, but I could wait a few months and basically have no budget.
I've had my eye on the JH16 Pro's. What should I do? 
My current cheap headphones for portable use are about to give out, so I may just order some cheap $50 in-ear klipsch image headphones in the mean time.

The way I see it, if you're willing to spend 600 now, but are willing to go higher, then just wait till you get something you really want. This way you don't spend the 600 then turn around a few months later wanting to upgrade or wishing you had gotten that newer or higher model. If you really need a headphone now, get an entry level can like a grado to hold you over till then.

The Sony EX1000+ZO, Westone 4, PFE232 and AMPs like T3d, PB2, E11 are recommended.

Get the RE0s and become a believer in dynamic drivers! it puts my other headphones to shame. If it weren't for this pair I would have always gone with the "just throw more money at it approach" in search for a better sound signature. These are one hell of a headphone after it burns in, it's an entirely fun detailed beast to be reckoned with. Pair this with a fiio e11 and bass boost it to your preference. Just for reference I own a pair of Brainwavz b2s, ultrasone prolines 750s, ue super fi 5 pros at the moment and sennheisers IE8 from an authorized dealer of course.