Tapes did sound a little better new, because they hadn't been worn by the magnetic heads. Cassette tapes are technically rated for hundreds of plays, but a lot of us would copy tapes onto blanks and listen to those.

The problem here is that the commercial tape has just enough tape for its longest side. Once you figure that out, you copy the longest side first. Then you carefully disassemble the blank tape and unspool the remaining tape, and cut it off, but you leave a couple inches. You then tape it to the spool. Now your copy is just as long as the original tape. (You might also record "bonus tracks" to fill the space.)

We put a lot of work into tapes back in the day. I remember there were two brands of blanks I liked. I liked the case/shell of one but the actual recording tape of the other. So I would buy two ten-packs, and disassemble them two at a time (one from each brand) and swap the innards. They were like $9-10 and $10-15 each (for ten-packs) so my cost would be around $25. A friend of mine would pay me like $5-10 for the bad/bad tapes. And they weren't really bad. They were just not as good. He also bought a lot of tapes (like with music) and I'd copy his. Neither of us really had the better or worse end of it. Really, we were just bored most of the time.