So today I went out a bought some CD's at a used CD store and listened to a couple in the car and it was by far the best listening experience I've had in a long time. Then I went to target and bought THE Discman that they had and when I got it home and tried it with my AKG K52 headphones it really didn't sound so great. Tried my earbuds that came with my S7 and , as expected, not very good either.
I have a the headphones I mentioned above and then a makeshift 6 or 7 (I have the center speaker turned off) speaker setup in the unfinished basement where I have my guitars and random stuff. It consists of 5 panasonic speakers I got for free from someone who had a DVD home theater in a box system that the DVD player broke and two 1970s panasonic speakers; These: .They all are connected to a newer Sony receiver that my roommate wasn't using. Its pretty wacky and doesn't sound very good. Maybe if I had a subwoofer and used either the old speaker or the other speaker set it would be better. Or maybe its all just junk.
In another room we (they really belong to my roommate) have a Sonos system. Two play:3s and the sub. They are kind of new to the house and sort of what propted me to start investigating my this subject.
Another room has the home theater setup. it's a 5.1 Definitive set of bookshelf speakers.
And in my bedroom I have a crappy Vizio sound bar subwoofer combo. Its not bad for TV and stuff but totally lousy for music listening.
The next thing I'm going to do is get some good headphones. I think theres enough speakers in this house, haha. I'd rather the headphone because then I can move around the house and go outside and stuff and I don't have to worry about bothering my 2 roommates.
After that, I'll tackle my itunes. I should clarify that I know now that you can rip CDs at high quality, but when I added most of what's on there I didn't know any better. I'm turning 30 this week and a lot of it comes from when I was a teen or early 20s. Probably some Napster and Limewire content on there too. I used to always be making CDs and then I would loose or scratch then and the whole thing was a mess.
I use pandora, spotify(paid), I watch a lot of youtube. Part of it is I miss putting on a CD and actually listening to a whole album.
There, I think I addressed everyones questions, did I not?
You seem to be trying to put lipstick on a pig.
First, a Discman isn't made to sound good, it's made for convenience. The first ones were pretty good, but they cost $300 in 1983 dollars so, you can adjust for inflation to find the equivalent. They were built far better, the circuitry was far better, they sounded much better and part of the reason is that they didn't run on a couple of AA batteries. You could use the best headphones and it still wouldn't sound great.
I hate to rain on your parade, but there's an issue with your speakers. That's an ad and it's wrong. I have never heard a pair of Thrusters that impressed me. I would recommend hitting the local thrift stores and Craig's List for something better. Older Infinity, JBL, Polk, EPI, Advent, KLH and many other brands can be had for a decent price.
WRT your basement room- if it's untreated, it can't sound good. It must be brutal when you play your guitar, if it's electric and you play it loud. Been there, hated it. Put up some moving blankets and try to absorb some of the sound.
The Sonos Play 3 and sub sell for $299 each and $699. You're comparing an old pair of speakers with new ones that sell for close to $1300. HTIB speakers aren't made for good sound, either. Again, it's simple setup and convenience.
If you want to use headphones and have internet access, I would recommend using the receiver (pick the best-sounding one) and look for a better set of speakers. This way, you can take your time and build something better, from the ground up. For portability, rip your music at the highest res possible and, while it will limit the number of songs in the music player or phone, it will sound better. As long as you have internet access, you can move around.