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. 

A,
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.

B,
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.