relaks
... if you are going to collect recent shiny issues to play on your new TT, just forget about outperforming a good digital source. Simply because this "analogue" record is a conversion of a digital studio recording ...It isn't that simple. That's because many commercial CDs and digital files have been substantially compressed as part of the Loudness Wars, while an LP may be given kinder treatment and have a wider dynamic range. Digital often doesn't take advantage of its theoretical technical advantages.
... a TT is a major money pit, buying it is just a beginning, and for most the very nature of a TT will lead to tinkering and upgrades ...Not necessarily. If you buy a good high-end turntable and pickup arm, future upgrades won't be required or even necessarily advantageous. (Although you will have to replace your stylus or phono cartridge every so often.)
I had several DACs in the last 20 years - Trivista, Reimyo, Naim and some other names I don’t even remember. Now I have Innuos ZEN mk3 + Aqua La Voce S3 as my main source ...Hmmm, you make digital sound like a money pit.