I will always have a place in my heart for anolog audio, vinyl and such with tubes glowing

(such depth/warmth with, to my ears anyway, a PRESENCE that I'm striving to match with digital). With the right dig equipment -and no, it need not be over the top expensive!- I'm finding that it's possible to achieve a convincing and pleasurable audio adventure, and this leads me to my question/advice seeking.
Currently, I have a FLAC app running on my iPad, and hence the majority of my music collection is in FLAC. I do believe it's certainly better than .mp3/.aac running @ 320kbs, perhaps not by a stunning margin, but still superior. On the XPS 630 desktop w the ASUS Xonar ST, the difference in quite noticeable.
My reason for switching to .AIFF over ALAC from FLAC would be as follows: .AIFF compatibility with iTunes, and .AIFF's supposed better (but possibly negligible) performance over compressed ALAC. I suppose, why not give your sound every practical (ah, that pesky definition of practical!) advantage in terms of quality. Does this sound like it makes sense? I'm a bit of a newbie, I admit it

also any advice on maximizing sound quality from the iPad2? Thank you all very much for all of your time and good advice!