Confused: Should I Upgrade Cables or Amp first?

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.

marktomaras-- thanks for your encouragement re: going disc-less. I will probably be compelled in time to follow your advice but I guess I'm old fashioned... OK-- maybe just old, as in an old dog and new audio tricks. 
Adding a quality DAC would be the easiest thing to incorporate into my room at this point. 

stereo5-- I welcome your positive remarks about the Halo, especially in comparison to a tube amp. I have come across many recommendations for the Cronus as a step up from the Jolida. I've never owned a Stereophile class-A-rated component and having read many enthusiastic reviews of the Halo, I'm excited to check it out, even though I know there's no guarantee it'll be the proverbial cat's pajamas. in my system. If it's not, I will, no doubt, be back here, asking for recommendations for DACs and Subs. 

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).

A subwoofer doesn't have to be large, they make small ones too. And placement can be less stressful than regular speakers, since lower frequency notes are not an easily detectable source.

I had my wife accept a new "end table" in our living room. It's a larger subwoofer ((2) 12 inch woofers), but it is just basic black box. It is placed between our chairs, and has a cloth doily on top with a lamp and books. No one knows it is a subwoofer unless I tell them.
 I've seen subwoofers that have just one 8 inch woofer, they should be able to be easily hidden.

This post is getting more and more interesting!  From cables to amp to speakers to DAC to subwoofer!  You have a stack of cash set aside for a considerable upgrade, and all of the options and opinions on this thread hold water.  Very tough to decide indeed.

This is a very exciting position to be in for a music enthusiast, especially as you say that you want to avoid the merry go round.  Now more than ever when reading the posts of my fellow audiogon members, I am wracking my brain, what would I do if I were in his shoes right now? What if I had to decide at this very moment?

As I re-read the post, I would eliminate a cable upgrade at this point. As you want the most significant change for the dollar, I think you will be better served in another department at this point.

A subwoofer will no doubt make a large difference in the sound. My previous speakers were monitors, and I added a sub to accompany them, with excellent results.  I dialed it in so that I could barely notice it was there, until I powered it off, and the difference was subtle but dramatic, if that makes sense despite the contradiction in terms.  I used a Wisdom SCS sub, which is thin, can be placed in unconventional locations, and is within your budget (the dealer I traded it to may still have it if you're interested).

DAC technology changes fast, and I don't see that changing anytime soon! Imagine when the iPhone will stop being upgraded on an annual basis... Probably never!  That said, you seem reluctant to upgrade your digital, and seem pleased with your CD player.

Unless your room is large or you play your music very loud, I'm not sure an amp upgrade will make a considerable difference in your listening experience with your speakers.  Of course there will be a change and of course it will be different, but the speakers don't have huge bass drivers and are pretty sensitive so the tube power you do have probably sounds pretty darned nice.

Whats left for that big upgrade?!  Speakers, being the end of the chain probably make the most difference, speakers and the source.  I would see what your monitors are worth, add that to the stack of cash, and evaluate what that sum can purchase in the used market.  See if there is a 3-way speaker with high-ish sensitivity of exceptional quality, at or above the quality of your monitors, and, one that fits in your space.  This research will allow you to decide if the speakers are the correct path.

if not, and the subwoofer idea is not exciting you, that eliminates quite a bit!  But, we left something out.  You mentioned CDs, but did not talk about any other sources.  One of the biggest things I have added to my system of late was a subscription to Tidal hifi.  4 million albums at uncompressed cd quality. It is unreal.  I can read music reviews and then immediately listen to all of the new music in the world as if I had all of the CDs!  It is very significant.  Perhaps you will consider adding a component such as the blue sound node 2 for $500, and getting a subscription to Tidal hifi.  That will be a very Very noticeable change!  It has an on board DAC for now and the ability to use an outboard DAC should you go that way.  You can still play your CDs on the Jolida and play Tidal on the node.  If you adore the experience, you may upgrade to a stand alone DAC in the future, and you will still have funds set aside to do so, perhaps even a tube DAC.

If you have any vinyl aspirations, $2500 is a fine entry, and I can tell you that I love spinning my vinyl more than my digital.  I love the experience and the sound - the analog in my system sounds better than digital. 

So, to sum up, I would be looking at a speaker upgrade, adding a sub, or adding Tidal via Bluesound Node 2 (or similar).  You should be able to add a sub and Bluesound / Tidal.  If you have any vinyl  thoughts, I'd be happy to lend my two cents there, as I believe an addition of an analog rig would also add a lot of addional musical enjoyment!