Where do I go from here?

The VPI Classic sound great. But the cartridge depends on your tastes in sound. Really detailed or musical? I love musical, so am really attracted to Van den Hull and Koetsu. They are musically oriented. 

The choice to go straight to streaming is the right one today. 
 

Streaming can sound better than CDs and equivalent or better than vinyl… but it depends on the price range. Vinyl wins in the <$20K digital leg area (meaning, you have to pay a premium… say 20% more for digital to equal vinyl… ((streamer + DAC vs TT + Phonostage). Over that, you can get equal sound quality for about the same money between digital and analog. 
 

My rule of thumb is the investment in carefully chosen components should be around Streamer = DAC = Preamp = amp… But about 30% more on speakers.

I am hoping this helps point you in the right direction. Given the age of your equipment, you might value it at 1/2 original cost.

Price isn’t everything, but it is a good way to think about how to invest in components to shoot for a very complementary set of components where no component unnecessarily holds back the system.

I had a pair of Acoustat 2 + 2’s in the late 70’s that simply put me permanently in the audiophile camp and began my lifetime pursuit.

Have a look at Linn. They have some very good sounding units from streamer / DAC all the way to everything in a single box. They sound stunning.

OP,

Whether digital or analog sounds better these days is entirely a question of what equipment you are using. You simply must find the right equipment and you can get the full analog sound from streaming. Just because you compared this and that does not generalize to analog vs digital. Careful choices in equipment will bring either format to the front. Streaming has sooooo many advantages it is worth the effort to put together a great digital streaming leg.

My analog leg and digital sound incredible and basically the same. It took a lot of work to get there… but well worth it.

😊👍