Looking to first time DAP buying advice after a couple weeks of researching on my own

[kapple]

Hi,
 
I am looking to replace my iPod Nano 6^th gen. It was fine for me, but the power button no longer works.
As I am looking to replace that MP3 player, I am being exposed to the different DAPs of various price points. I am a newbie at this, and am looking for some advice.
 
I currently user Sennheiser CX400 ear buds. They have been fine for me thus far in terms of quality and volume.
I have a Bose SoundLink Color Bluetooth Speaker. This speaker also has a 3.5 mm auxiliary input. I would connect the iPod via the aux port when camping or outdoors listening with others.
 
Most of my music is live concerts that I download from archive.org, though I also listen to a bunch of CDs that I have ripped, encoded as MP3 160kbps (trying to conserve space on the iPod since it is always full).
 
I am seriously considering one of the mid-range DAPs instead of a cheaper MP3 player. I like the idea of listening to FLAC/24 bit recordings. Even though a lot of the concerts I download are not professionally produced, they are available in that format. I am also considering re-ripping my CDs to a better quality recording as well.
 
Some of the DAPs I am considering are the following:
Cowon Plenue D
FiiO X1
FiiO X3-II
Sony Walkman NWZA17
Sony  WalkmanNWA26
SONY Walkman NW-A35, once it is released in the US.
 
I was considering a few of the AGPTek models, but there seems to be issues with them that would drive me crazy
 
Another consideration I have is that if I am going to spend $100 - $300 on a DAP, I may need to upgrade my earphones/speaker at some point.
 
Options I would prefer are:
A lot of storage. I was always shuffling playlists on and off my iPod, due to lack of space.
Prefer built in storage, with the option to add more with a micro SD card.
Bluetooth would be good for now, since I have my Bose speaker, but is not a deal-breaker if there is not Bluetooth. There may be a reason for that (see question below).
Ability to create playlists, though I guess I could do the same with good folder organization.
I would like the ability to use speakers, as well as earphones. I am hoping to make this the beginning of my home stereo, which currently consists of my laptop and smart-phone (all my old stereo equipment is stored in my garage, the graveyard of sound).
 
So here are my questions that I hope to have some input from you all:
 
With these Hi-Fi DAPs, is Bluetooth a viable listening option?
If so, is there a minimal Bluetooth version any device I buy should have?
Are these DAPs designed only for headphones, or would they work with speakers as well via the 3.5 mm jack, or via Bluetooth?
If speakers are an option, does anyone know what type of speakers to buy? I am having a hard time with this one.
 
I really like the Sony products, except for the fact that they use a proprietary USB cable. The Cowon looks really cool too.  Not too sure about the FiiO at this point. Any other recommendations would be great.
 
I may come back with more questions, especially based on any replies I may get from this forum.
I appreciate any feedback or guidance you all could provide. I am really driving myself crazy shopping for my iPod replacement, and since that broke after 4 years, I think I will stay away from Apple products. 
 
Thanks,
Ken

 

[PurpleAngel]

  Most of my music is live concerts that I download from archive.org, though I also listen to a bunch of CDs that I have ripped, encoded as MP3 160kbps (trying to conserve space on the iPod since it is always full).
I am seriously considering one of the mid-range DAPs instead of a cheaper MP3 player. I like the idea of listening to FLAC/24 bit recordings. Even though a lot of the concerts I download are not professionally produced, they are available in that format. I am also considering re-ripping my CDs to a better quality recording as well.
Some of the DAPs I am considering are the following:
Cowon Plenue D
FiiO X1
FiiO X3-II
Sony Walkman NWZA17
Sony  WalkmanNWA26
SONY Walkman NW-A35, once it is released in the US.
Another consideration I have is that if I am going to spend $100 - $300 on a DAP, I may need to upgrade my earphones/speaker at some point.
Options I would prefer are:
A lot of storage. I was always shuffling playlists on and off my iPod, due to lack of space.
Prefer built in storage, with the option to add more with a micro SD card.
With these Hi-Fi DAPs, is Bluetooth a viable listening option?
If so, is there a minimal Bluetooth version any device I buy should have?
Are these DAPs designed only for headphones, or would they work with speakers as well via the 3.5 mm jack, or via Bluetooth?
If speakers are an option, does anyone know what type of speakers to buy? I am having a hard time with this one.
I really like the Sony products, except for the fact that they use a proprietary USB cable. The Cowon looks really cool too.  Not too sure about the FiiO at this point. Any other recommendations would be great.
I may come back with more questions, especially based on any replies I may get from this forum.
I appreciate any feedback or guidance you all could provide. I am really driving myself crazy shopping for my iPod replacement, and since that broke after 4 years, I think I will stay away from Apple products. 

 
Some DAPs come with a line-output function, which is what you would want to use for connecting to speakers (self-powered) or an amplifier.
The headphone output (headphone amplifiered output) will also work for connecting to a speaker/amplifier, but line-output sends a better signal (to the speaker/amplifier).
 
Unless a source is professionally recorded, I doubt a FLAC version is going to be noticeally better then a good quality mp3 version (best guess).
 
Check out the Xduoo X3 DAP, same CS4398 DAC chip as the FiiO X3 Gen 2.

 

[kapple]

Thanks for the feedback PurpleAngel, I appreciate it.
 
One other feature that is a must have for me is gapless transitions between tracks. 

 

[sciman111]

Have you considred the Fiio X5 Gen 3.  It looks very appealing for the price.

 

[kapple]

Thanks sciman. Right now considering either the Fiio X5 2nd gen, or Fiio X3 2nd gen. The X5 3rd gen is a bit pricy for me, though I like the idea of having Bluetooth and WiFi available. What is holding me back is that from reading on various forums, I am not confident that gapless playback works flawlessly for both lossless and lossy files on those models.