Digital direction needed

Should I just start with a Dac in this chain?

Not really possible to give an informed opinion here without knowing the rest of your system. 

I burn my CDs to the laptop and that is my control center.  The Oppo has balanced and RCA.  The balanced goes to my Pass labs 150 and on to the Sonus Faber's Cremona Auditors.  The RCAs go to the Primal luna Dialogue premium and on to my Lawrence Cellos.   The speakers are in different rooms and there are many times - I like running them both at the same time.  I, too use the Oppo remote from my IPAD.   I've loaded 100lbs of CDs to the laptop.  I didn't count them, but since I boxed them - I weighed them.  :-)    I used Tidal for a bit, but I have so many CDs the monthly charge seemed excessive.  

I do like the set-up.   The Oppo - I have had a long time and eventually it will bite the dust.  I am just looking at options down the road.  Something to chew on - Options I should consider. Things I can improve on.   I will look at the Boss...

Your Oppo might last years.  If you like your current setup, relax and listen to music 

You’re pretty much doing what I’m doing except the CDs are on a Mac Mini. I rip using XLD and use BitPerfect for playback.

However, both XLD and BitPerfect seem to be getting long in the tooth and I’m having occasional issues with both.

So recently I ripped using plain iTunes and playback using iTunes alone. Guess what? I don’t hear any difference. Gasp!

Anyway, I get the impression that my Oppo is pretty well built so I’m not expecting any impending failures and as long as it keeps running it will remain my primary DAC and CD player.

I’m not inclined to chase ethereal improvements that with my ears are more likely to be my imagination or mood anyway so I’m sticking with what I have for the foreseeable future. And that in itself is a good feeling.