Stuck in a digital age rut/ problem and need some Help!

Hi everyone about 5 years ago when I was just 18 i started my audiophile journey. At the time digital was the rage over the vinyl comeback, When I was 18 I bought a cary SLI-80 integrated amp and a new mac book pro in 2012. I spent saving up the next two years for a digital component/CD player. That would stand the test of time like my dads 20year old teac cd player which still works till this day. I read all reviews on magazines and had a large collection of cd's and hi res iTunes files. This was when the idea of DSD was only on SACD not computers. I heard such good things about SACD I wanted to get into it. So I had the choice of 2 cdplayers/dac's The marantz SA11s3 which supports Mac's through usb and plays SACD for $3700 new. Or a new dealer demo Cary Audio SACD-303t pro $6500 for $3500 which supports only PC through USB and Mac through toslink, and plays SACD, and HDCD. With the options of tube or solid state output.
Being young and innocent, I bought the cary for the cheaper price and matching my amp. Well Its 5 years now and have spent many hours of enjoyment and out standed by the performance of my beloved 303T.  And now my CD player is not reading new discs most of the time and disappointed it didn't last me at least 10Years.. And my Mac is almost lived its life the toslink is shot and its a $650 fix and none of the new macs support toslink on top of that. And price of Apple Mac's in Canada have gone up by$1200. Also priced out parts for the CD transport and sacd /CD chip board portion of player is going to be $1500 USD, plus labour and shipping/ duty and $200USD bench fee. So I'm stuck in a rut right now, also digital play back has advanced so rapidly now.
 Should A guy go back into a junky Microsoft computer to run into the usb port, and get the transport fixed. And some people tell me it might still not be fixed, after the fix.

Or my second option buy a new Chord 2 Qute dac for $1600CAD and save up for a new cary cd player with the fall of the Canadian dollar. Thanks to Mr Trudeau and sell my 14 SACD's?
What are your guys thoughts?
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" Should A guy go back into a junky Microsoft computer to run into the usb port, and get the transport fixed. And some people tell me it might still not be fixed, after the fix."

Macs are not what they used to be. Now that Apple is doing really well, they kind of act like the new Microsoft. They have a take it or leave it attitude, and they're not doing much to keep OSX as competitive as they used to. Microsoft, on the other hand, realized the mistakes they made with Win8, and are actually trying very hard to set things right. Windows 10 is solid. I have no problem using it for music.

The bottom line is this. You can spend $500 for an HP, Lenovo... laptop, or $1500 for a Macbook, and install jRiver on both machines. Providing both machines are set up properly, they should sound the same, or very close to it.
CD players do seem to fail due to the transports as a weak link, so why not look at DAC's as a complete solution, rather than a bridge?  I switched from CD players to DAC's 3 years ago, and I have definitely enjoyed improved sound (OK, the DAC's clearly were better than the DAC in the CD players), and I really like the benefit of ease of use that a computer server brings.  My 2 cents.