[TRapz]

For the past couple years, I've mainly used Windows Media Player with WMA Lossless files or iTunes with mp3 files (rarely). Over the past year, I began collecting CDs and ripped them mainly using WMP. I also tried iTunes (ALAC and AIFF), and on WMP, mainly WMA Lossless and I tried some WAV. In other words, my music collection is all unorganized, and I'd like to fix that. As much as I like WMP, I want to try to use FLAC, as it is supported on more devices than WMA Lossless and is more compressed than WAV. ALAC and AIFF aren't options, as I did not like iTunes very much. What I'm looking for is a media player similar to WMP but that can play more file types (FLAC preferably). These files will mainly used on my FiiO X1, though sometime in the future I may use them off of my computer with a DAC/amp. Some stuff I want/some questions:

1. Automatic, accurate tagging like WMP
2. Similar layout to WMP- I really enjoy the layout of Windows Media Player, and would enjoy something with a similar layout
3. Easy to use, but more options
4. Should I use FLAC files? I've heard FLAC is widely regarded as the best, though I'm not sure for what reasons; I do know that FLAC is supported on more devices than WMA Lossless.
5. How do I use FLAC files? I'm 99% sure something must be downloaded for FLAC support, but how do I get it running? Should I download a media player first?
6. I believe I've heard of different levels of compression for FLAC; what is this (I assume it decides how compressed the file is) and how do I use it?

 
Some media players I've heard about:

1. MediaMonkey: Looks easy to use, supports FLAC, like the layout
2. Foobar2000: Seems somewhat complicated but supports FLAC; don't like the layout much
3. MusicBee: Supports FLAC, seems easy to use, layout seems great

 
I'd love some recommendations for media players, and also file types if anyone believes that FLAC is not optimal. Any responses are very welcome and I thank you for your time reading and responding.

 

[Sattelight]

Foobar is great for me. Very customizable so that you can adjust it to your personal preferences. It does seem complicated at first but it is pretty simple after a little fiddling. Foobar also allows for installation of of components that can really come in handy. Dynamic range meter, split equalizer, resampler, ABX comparisons to name a few that I have found extremely useful
 
To play flac files you need the codec installed. If you use Foobar, they have a codec pack that you can install with it that will allow you to play pretty much any of the common file types. With regards to compression, the only difference is how long you want to wait for your files to be converted. Less time = bigger file. If you want smaller files it will take a little longer but they are all lossless so they are sonically equivalent.
 
Whether or not flac is optimal really depends on you. Personally, I can't tell a difference between flac files and lossy files like mp3, aac, opus etc. I rip my CDs to flac because I like the idea of having lossless files on hand but if storage space is a concern, as it is on my sansa clip, I'll convert those to 200 kbps variable bitrate opus files to save space. 
 
My recommendation for you would be to try all of the players you have listed and see which one you prefer. If you want to keep your files in a lossless format flac is definitely the way to go as it is supported by just about every device except apple products otherwise I'd recommend variable bitrate mp3s as those are also widely supported. 
 
hope this helps