Upgrade path question. Upgrade analog or turn to digital?

I am running a full analog rig and my beloved cartridge needs service soon (6 months about) so I am wondering if I should sell the analog rig (tt+phono+lps) and rather buy digital source. I am planning to upgrade it later if I am not going digital. 

I am satisfied playing lps, I do it when I can focus on music, but sometimes it`s tempting to have the same quality, just a button away. I can afford either the digital or the analog upgrade and I don`t have the space for both. I am thinking about two scenarios. 

Change the diamond in the Ikeda, rewire the tonearm, change the bearing, add a DS Audio ION-001, max out the VPI Classic 1. It`s sittin on a Shun Mook maple board and heavy sandbox right now, looking for a serious platform north 2000 dollars used or that money goes to the phono upgrade.
Upgrade the phono later, what I save on the digital goes here. I am hoping for a used Aries Cerat, but would be happy with other OTL solutions.

I sell the analog rig and going digital. I was thinking about to buy a streamer north 5K used and either a ESOTERIC D-02X, Aries Cerat Kassandra II, or similar. 

I am planning to upgrade the integrated amp either way, the room treatment almost done.

Or a C version,

Gryphon Diablo 120 with DAC and call it a day.





Why are you against upgrading the phono, the amp and the platform altogether? The tt upgrades are coming quite inexpensive so that makes sense. 

My feeling is that you can always go digital in other audio in your life, but vinyl is what you have set up your system for. regardless of sound quality either way, the physical aspect of vinyl has been part of the catch for me. Same with coffee. I grind my beans with a hand grinder. Have had the same grinder for 35 years now. In my mind, why would I put the beans into very noisy electric grinder and ruin the mood to begin with? 

If you decide change make sure you listen to a digital system you really like before you go that route. Whatever you decide to do I find that room correction software like ARC from Anthem/Paradigm, Audyssey or Dirac is a must have, not a nice to have. I have a very well treated room and room correction software works better in that environment. It can't make magic out of a bad room, just dial in one that is already decent.