Took the DAP plunge - now need help to figure out how to use it ...!

[HesNot]

I just picked up a Pioneer XDP-100R (black) as my first foray into a dedicated DAP which should arrive sometime next week.   Just to add some color to the intended rig, my best headphones are NOCS NS-800 v2 IEMs and a pair of Bose OE2i that I picked up on 50% clearance - I like the NOCS sound overall but admit to being less enthusiastic about the Bose (and I'm not a Bose basher - I won't buy their stuff full price - but my soundsports do what they are supposed to do rather well as does my soundlink mini) - just a bit too bass heavy and not enough top end clarity.  I'll upgrade at some point next year when I've had time to sort through the signficantly more difficult and dense world of headphone/IEM choices.  
 
I have a Macbook Air and my primary listening will be at least initially to CDs ripped onto the Mac then transferred to the XDP and streaming Tidal (one reason I got the Pioneer instead of some other options, iBasso FIIO etc...).  As an aside I wonder if I ought to have just gotten an iPod Touch given my Mac base and primary CD source plusI've used other iPods, have an iPhone 6 and am familiar with the interface and controls... but at least the Pioneer gives me some more options long term (I have used a number of Nexus devices so I'm pretty well versed in Android as well but have no media tied to that ecosystem)...  Anyway - I once loaded most of my CDs into iTunes on a different Mac, now dead (ultimately to be replaced and restored via time machine backup), but it was some time ago and I did not pay attention to the format I used so likely AAC given that's the default so I'll likely end up re-importing them into my newer Macbook Air for use with the XDP.  
 
So my basic question - is how do I go about importing my CDs and then transferring to the XDP?  Specifically - I believe it is not possible to circumvent iTunes when importing CDs so they'll end up in the iTunes library.  I believe also I'm limited to ALAC natively, but is there any reason with CDs to bother with a third party FLAC add on/app which I think exist?  Once music is in iTunes I need to transfer to the XDP - there is an XDAP link app for the Mac which apparently can be used to recognize the iTunes library and then transfer to the XDP, but are there methods that are better or superior in terms of quality/usability/flexibility?  I thought I'd read about other appls that integrate with iTunes both on import and transfer but how to use them or why you'd want to are a bit unclear.
 
Lastly - I intend to use the XDP in my car - at the office - and also as one source (streaming since I can just play my CDs!) on my home system (Nakamichi SR-2A receiver, JVC XL-M405 CD, Thorens TD280 TT and Cambridge Soundworks Ensemble speakers - yes I'm an old 80s early 90s audio guy).  In the past I've used an Airport Express as the connection between any streaming media and the receiver using a 3.5mm to RCA cord between the Airport Express and receiver but is there a better method?  Just connect the XDP directly to the 3.5 to RCA cord?
 
My apologies for the very newbie questions - many thanks!

 

[ProtegeManiac]

Not sure why you'd even bother leaving iTunes considering those who are in it have a hard time getting around to learning something else. Even using Android phones doesn't guarantee you'll find using DAPs any easier as these are also simplified as far as file association, organization, and tagging are concerned so they don't lag behind Apple in sales considering these are also mainstream products unlike DAPs, even if they're made by a company like Pioneer.

 

In any case, you already purchased it, so the first step is to get rid of iTunes and download something else, like MediaMonkey. This needs to manually select the folder/s that you want to add to its library, unlike how even if you put up a separate folder with FLAC (a format iTunes can't even read), iTunes will recognize these as audio files and associate them only​ with iTunes (despite not being able to read it), and then MediaMonkey can't access the same FLAC files no matter how hard you try. It's like if the Ptolemies/Romans/Byzantines marched into Baghdad or Persia, hoarded the scrolls, and then won't let any Semitics or Persians near it even if they can barely read what's on them. You then end up with iTunes with files it can't read and MediaMonkey with files it can not access. So, I repeat: GET RID OF ITUNES and if you have an iPhone, just use Spotify on it or use iTunes on a separate computer as the one with MediaMonkey or Foobar or whatever.

 

Next, re=rip your CDs using MediaMonkey, Foobar, etc, making sure to check if it's ripping to FLAC or whatever other format you prefer, as well as proper file names and organization, ie, make Artist Folders automatically, then to make everything else easier, you manually organize them into Album folders, otherwise having these programs do several layers deep of organization folders will make filenames too long. Next step in the entire process of confusing Apple users is to check and edit track tags. I do it manually - first step is to batch-edit the tracks from one album to have the same album title, genre, etc; if it's embedded as on newer CDs, I check and edit anyway as sometimes the embedded tags end up confusing anything that doesn't have its own version of the tags in iTunes music store to not confuse iTunes player. Also, here's one tip - do multi-disc albums as one album by editing the track numbers of CDx to pick up where the previous disc stopped, then batch edit them all and delete the "Disc_0x" suffix that auto-tagging does, since...well, they won't be on a disc anyway.

 

After organizing your folders you have to open up Explorer (or whatever the heck mountain operating system calls it), right click on the entire audio library (for your first set-up; later ones will just have the specific folders going into the specific destination folder), then go into the destination folder, right click again, then left click Paste. The destination folder will vary depending on what DAP you bought and what works with it best. Some require formatting the SD card, leaving it in the DAP, then hooking it up via USB, and then you search for the SD card as it is inside the player in Explorer, and then you either run the DAP's read protocol or reset or whatever it needs so it will recognize the files (others might do this process during file transfer). Others work more like Android phones - format the SD card in the DAP, then you can hook up the DAP to the card reader on your computer (or whatever dongle or overpriced, metal shell adapter you have if you have a MacBook), copy the main audio folder and all its contents in there, put the card back in the DAP, then power it on and depending on how it works, you might have to run the library scan protocol.

 

If all that seems tedious, just ship the DAP back before you cut any seal on the box (ie it may be wrapped in plastic or has a sticker on the lid that prevents it from opening), that way you only get charged the minimum in return fees plus shipping, and then order a DAC that works with a smartphone.​

 

[Monsterzero]

I dont have your DAP,but I have 2 FiiOs and a Ibasso in my home and all three play both FLAC and ALAC,and none are a TOTL DAP...first I would check if your player supports ALAC(it should)before trying to decode from ALAC to FLAC.

Secondly many DAPs support drag and drop...simple as that.

As far as creating folders/playlists,etc...that is a DAP to DAP thing....some have more features than others,and frankly im too lazy to look up your incoming player,but you shouldnt be.

Im pretty liberal when it comes to folders...I create a folder for a genre,take "Blues" for example...and all the blues I have goes into that folder...if you wanna get more creative make a sub-folder for Muddy Waters or Buddy Guy and stick that in the Blues folder too...once all your music is organized on your comp,put it all into one big folder called "music"...drag and drop the music folder and walk away...give it several hours to a few days depending upon how much music you have...once thats done all your folders and sub-folders should exist on your DAP as you created them. 

EDIT: try to do as much organizing,folders etc on your computer as opposed to your DAP...creating playlists on the other hand is another story...i have yet to find a  DAP that will allow me to import a playlist...so i just use my folders as a "playlist"

 

[HesNot]

Thanks for the insights everyone - yes it does sound a bit tedious but... I suppose we'll see how much patience I have for better sound!  I think I have a fair amount - also need to check out the OSX dap link-x software to see if that eases the process.  The XDP does support ALAC so perhaps there is a way to still use itunes with this player (since I do still use a Nano at the gym).
 
I have avoided a phone as a standalone music player mostly due to storage issues since my iPhone has a range of apps I use regularly as well as my work email... 

 

[ProtegeManiac]

 
I have avoided a phone as a standalone music player mostly due to storage issues since my iPhone has a range of apps I use regularly as well as my work email... 

 
Spotify isn't all that bad though, and more so if you're not doing any critical listening on the go. I only have locally stored files on my Android since it's the music server in my system at home.