My iPad is under 1.5# and I have no external hard drive. My little boombox is also fairly small the connection to the iPad is wireless (Bluetooth). The boombox will even last for six hours without being plugged in. You undoubtedly have a rig with better fidelity than mine but for use when travelling, I like the simplicity of what I have got and am willing to accept some compromises. When you said "laptop" above, I envisioned something the size of my portable workhorse with its 17 inch screen (it stays home -- I am not working on vacation) instead of the considerably smaller device you actually have. Certainly separate speakers would sound a bit better, but then I would have more pieces and probably some wires too.
The age thing is real -- I have never been to a loud concert or other really loud venue without good earplugs, but yet the highest frequency I can hear is now about a third of what it was when I was, say, in my early 20's. Even with my deteriorated hearing, I can detect a difference in sound quality between my old CDs and a lot of the newer ones. Since the odds on are that you are considerably younger than I, I am sure you can hear the difference better. The method I use for saving my tracks is virtually the same as the old CD specs. That is what I meant by "near CD quality" -- stuff that is old like me. Of course, even when ripping CDs into a format with the same specs, there is a slight loss. So be it. Also of course, ripping at a higher bit rate than the original does not improve anything -- it just means you lose less. Since I have a 64 Gig limit on my iPad I wanted something that would allow me to carry virtually all my best music and not have to swap, ever. That also was behind my choice of formats.
I do not think we disagree on any of the technical stuff. Your method undoubtedly sounds better but mine better fits my purpose and desire just as yours fits better for you.