CDP or DAC?

Seems to me you'll have greater flexibility in terms of pleasing your ears if you go with separates.  DACs can vary enormously in their presentation. 
John Darko once used a "cake" analogy, contrasting those who prefer to "taste cake" to those who prefer to "taste flour, sugar, butter and eggs". 

If you're used to vinyl, you may find a good many DACs are too clinical in terms of breaking the music down into its constituent "ingredients". . . or, you may find their ultra-resolution very exciting. Who knows? You'll have to demo some and see. If you know you prefer to "taste cake", I'd second the R2R recommendation.   

BTW; like two other posters, here, I use the Moon 260DT (transport version). 

Getting digital to equal the quality of a $15,000+ analog set up is not an easy task. You must do everything right. You can begin by tossing the idea that you want to play physical disks. Start ripping your CDs and SACDs to a hard disk. Not only better convenience, but better SQ and a saving of cash you will need. Do research on the best DAC for you. Sigma delta chips, multibit chips and discrete D2D devices have all been proven to make great DACs when properly implemented. Some are more detailed; some are more "relaxed." Choose the flavor of the month if you wish. Since you’re an analog person pay careful attention to the analog section of the DAC. Discrete sections should outperform those based on chip op amps. Finally, just as a TT has to feed the phono pre a good signal from the LP, you will have to feed quality bits from your HD to your DAC. That will take research too. Good luck! I did it. You can do it.

get a sony scd-1 vsei modded level 6

or a modwright modded sony or marantz s-cdp w tube output and tube rectification

spend the rest on more cd’s

good luck n happy listening

Listening to my Sony SCD-1 vset modded Level 5+ tonight and it always puts a smile on my face. Listening to Dark Side of the Moon on SACD is always a treat.

Another +vote for CDP. And SACD player too!

Happy Listening!