Ultimately, I want to be able to judge whether it is worth spending any more on my vinyl hardware, or stick with digital.
You can play leapfrog with you vinyl and digital front ends for the rest of your life. Upgrade your vinyl system and it will outperform your digital. Then upgrade your digital front end and it will outperform your vinyl rig that you just upgraded, etc., etc. You get the idea.
Just figure out what you want to listen to and dump most of the money into one of the two or achieve lesser performance and have both. If you have unlimited funds, build two state of the art front ends.
If you like records that aren't available in digital formats or if you listen to a lot of albums where the vinyl mastering is much better than the digital versions, then you kind of need a good analog front end. If neither of those cases apply to you, then it probably doesn't make sense to mess with vinyl unless you just like to learn about and play with TTs, carts., and phonostages (which is a totally valid reason to have a TT in my opinion).