Things break, that's life.  No matter how simple you keep it something can always break.  The fun of this hobby is upgrading.  There is always a better headphone or amp or DAC.  To not start somewhere no matter how small, seems to be a mistake.  You gotta jump in sometime.

Separates always sound better but you need a bigger budget.  Used is a way to save but still your budget is not in the range to set yourself up completely.  My suggestion then is to buy a nice headphone amp that has enough power to run efficient bookshelf or desktop speakers.  Use the amp with...

I am about to upgrade my old and true ONIX XCD-88 CD player, which is similar to the Music Hall CD player of a few years back.  The unit is playing strong, although it may not be current any longer, but I love it and thought to refresh its sound I would upgrade the OP Amps.  A number of years...