Confused: Should I Upgrade Cables or Amp first?


I currently have very long runs of Audio Art SC-5 speaker cable (about 20 feet) that, due to WAF issues, are routed through holes in the floor, under the house. I use MIT AVT speaker interfaces, in an attempt to compensate for resistance.

Speakers: Silverline 17.5 monitors. Components: modded Jolida JD100 tube cdp and modded Jolida JD302 tube (EL34) integrated. 

I can afford to put $2500 into the system at this point. I could re-route cables through a wall and relocate components into another room, thereby dramatically shortening cable runs to 10-12 feet and enabling bi-wiring. I could also afford to upgrade all cables. OR, I could leave cables alone and upgrade amp.

Which is likely to produce biggest improvement? 
stuartk
marktomaras-- thanks for your input. The reason I have monitors is that I don't have the luxury of a dedicated audio space, and as a result, I needed to raise drivers above furniture in the livingroom.  Pardon my ignorance, but would the 50 watt Jolida sufficiently drive the 91db Silverline 3-way floor-standers? RE: source, I can't yet face the prospect of the time and monotony involved in ripping my cds. While I don't have a huge collection, it's definitely not small.  What about adding a DAC, instead?

Stuartk:  I have a Parasound Halo Integrated in my secondary system with Audio Art SC-5 speaker cables.  They are connected to Golden Ear Triton 2 speakers.  I listen to this system 90% of the time because it is in my home office.  It's a great match.

Previously I was using a Rogue Audio Cronus Magnum tube integrated and for my taste, I like the Halo Integrated much better.

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.