Dear jeffvegas,
The decision to where to invest/spend your $$$ is a very personal one - its what's makes you happy - how do you define you destination or your journey.
Digital music has matured to a music presentation all its own. There is little value in investing in a CD player - the best CD lasers like the swing-arm Phillips CDM4/Pro with German glass optics and 50,000-hr life are history. Better to burn CDs to FLAC or WAV and use a fanless laptop as a music player with free music player software such as MediaMonkey.
The current future (and as digital it is always subject to change), of digital music is streaming with the current business model of subscription service - how many streaming services will survive is debatable since I believe that many are not yet profitable, but something will survive. But, consider that if a Hi-Rez music file can be transmitted from a remote physical storage facility (i.e. server center) through 100’s if not 1,000’s of miles of combined fiberoptic and copper cable, through connectors, repeaters, amplifiers; maybe a fiberoptic to copper converter at your home to a router all using 1,000’s if not 10,000’s of circuits, processing by 10,000’s if not 100,000’s of lines of computer operating/BIOS/firmware code, and emerge at your home server bit-perfect be it a lap top or dedicated server, the whole argument of home hardware evaporates, leaving nothing more than the DAC. With the Benchmark DCA-3 (as an example - $1700 for DAC only) essentially being engineering perfection (with I believe a 5-yr warranty) its is plug and play; one and done. You cannot argue the life-cycle cost of digital music streaming.
Vinyl is anything but plug and play; one and done; it is not about convenience. It is journey with every step yield personal satisfaction and some frustration, all to get that uniquely analog music experience and presentation that no doubt there is the pride and the allegiance that one achieves from putting in the effort to get it right. There is a lot to learn and a lot to explore, and if you buy smart - there is a pretty clear upgrade path. If you buy the VPI Scoutmaster, first VPI still supports it, if you need a new arm pivot or a new motor they have it. There is an upgrade path to the heavier aluminum platter, different feet, the JMW-10.5 arm and base, the dual-pivot, and each one will improve incrementally the music which then drives you back to re-listening to all your vinyl albums, again and again. If you were to buy the Soundsmith Carmen MKII cartridge that is on-sale at Elusive Disk for $699 - this is an awesome cartridge for the money, easy to drive, quiet and they will rebuild it for $199. So, your cartridge life cycle cost is $199/1000-hrs.
Now, if you add up what I just discussed - DAC (Benchmark - new) $1700, Turntable/arm (VPI used) - $1500, Cartridge (Soundsmith Carmen - new) - $699, total cost = $3900, add $100 for turntable incidentals = $4000, right on budget with a 5 year plan for possible turntable upgrades.
Just one opinion, but I gave up on investing in digital and invested in vinyl for the very reasons just stated. Its your journey and its your experiment, make it your own.
R/Neil