Confused: Should I Upgrade Cables or Amp first?

91 dB sensitivity is quite efficient, so if your room is not huge and you listen at moderate volume levels, the Jolida 50 watt should be fine. If you have a largish room and want to be the memorex guy in the chair, you will probably need more power.

ripping CDs is really easy. If you did just 10 per evening and a few extras on the weekends (which is barely any effort at all), you'd burn through a good sized collection in a month.  Once you set up your settings and get the software doing its job, really all you do is put the disc in and press go.  Walk away, and when you remember to check in on it, the rip is done and you swap the disc.

You can add a DAC, but better to free up CD player funds and get either a better DAC with those additional dollars, or recycle some of that gear budget.

I can't tell you how liberated I felt when I sold my CDs to the used record store!  You can't beat your collection on a hard drive, plus a subscription to Tidal hifi, which streams 4 million albums at full cd quality, all tied together with a good music app like Roon, played through a high quality DAC.  

I really think that digital change or an upgrade in speakers will add the most bump to your system.  Or, perhaps not changing the speakers, but adding a high quality subwoofer to give you a fuller range experience, also possible to do very well with your budget.

Cables react differently connected to different components.  Finalize your system then experiment with cables.

@stuartk 50 wpc should be plenty of power for a 91 db speaker, assuming that the room is not unusually large and/or listening levels unusually loud.

Maybe what you are missing is a little bass? Maybe adding a subwoofer to the mix?
Otherwise I think your system seems fairly well balanced. Sure, you could get better speakers, then that usually drives you to get better sources, amps, cables, etc. The merry-go-round never ends for some.

If you are relatively happy, just enjoy the tunes and spend the money elsewhere.

jmcgrogan2-- yes, more bass would indeed be nice. The bass I have is well defined and relatively quick; it just doesn't extend down very far, as you have no doubt surmised.  Finding a place for a sub in our livingroom is the hard part (WAF). I get what you mean about the merry-go-round. Fortunately or unfortunately, the reality is; I lack the funds to indulge in that particular life-path!  The downside is that when I do have a little money for upgrades, I feel a great deal of pressure to make the most of my investment. No doubt this is a familiar enough scenario for other Audiogon members.

marktomaras-- my impression is that when it comes to DACs, the technology is changing rapidly. Schiit's DACs are, apparently upgradeable. Unfortunately, they charge a 10% restocking fee should one elect to return a component; this has, so far, kept me from ordering one to try. I have two friends with expensive systems who both have the PS Audio DAC that sells for $ 1200 (don't recall the name). I tried it in my system and it did wonders for female vocals but otherwise, it didn't blow me away. Also, it accentuated differences in recording/mastering quality from one CD to another. As I am more of a music lover than an audiophile, I'd rather have a system that's more on the forgiving side, even if I lose resolution.