well it seems like you have a good main source already so no worries there......you have an eye for an LOD already, no complaints there other than price. I really don't know how much an ipod LOD cost you, so you'll have to look around the forums to see if you can find a thread that talks about it.
Now, here is the part that gets a little tricky, the amp and your IEMs. The amp that you listed seems really good for the price, but personally, since your budget is so high, i would just say go for an arrow amp 4g. It'll supply you with the power you need, it's ultrathin to meet the form factor of your ipod, and it'll be future proof to some degree. The downside of this all is that the arrow amp is 300 dollars, not exactly cheap by any means. However, it's value to performance is what keeps people raving about this little amp in the forums. Completely your pick since you'll be the one forking the bill but nevertheless you should have this little amp on your radar.
For IEMs you really do have a wide range of IEMs to pick from. You can decide to get a cheap amp and better headphones or you can decide to get a future proof amp with cheaper headphones. It's all a matter of preference at that point because only you can decide how often you replace headphones or equipment. Regardless of if you get the 60 dollar amp or the arrow amp, i think the best IEMs you can start out with are the DBA-02.