I got my stereo back after almost 20 years!

As the subject says; I got my stereo back after almost 20 years.

The short story is that my mother in law came to visit and didn't leave until last October.  As she aged she started taking over the house.  My reading chair became hers and the family room was where she watched TV.  I've been listening to music on my computer, (with small stacked Bostons and a pawn shop sub) for almost 20 years.  It finally dawned on me that I could buy another stereo.  So for the past 5 months I've been cobbling together a system.

I bought a pair of Quad 2805s as I love the planer/esl sound and listen mainly to jazz.  They arrived with only one speaker working so I had them completely rebuilt and upgraded by Kent at Electrostatic Solutions.  My system currently is:

Quad 2805 speakers
Prima Luna Dialogue HP
Cambridge Audio CD transport
DacMagic 100

I ripped all my CDs to a Macbook using DBpoweramp and stream with Spotify.

So here's the dilemma;

I really can't hear much of a difference between Spotify, my ripped music on my Macbook or the transport.

I realize that the weakest links are the front end.

Here are my questions I need help with:

1. Should I buy a new DAC?  Something like the Schiit Gungiar (sp?) or PS Audio NU Wave?  Or would I be better off getting a network player that can also stream?  I do like running things off the Mac.

2.  I'm 64 and my hearing is obviously not what it once was.  If I upgraded would I hear any difference?  The downside of being 64 is not hearing as well but it may also be an upside as I could save considerable dollars!

3. I'm also 250-275 miles away from the nearest dealers and that presents a problem auditioning gear.  Also most dealers don't carry Quads. 

4.  And finally I am comfortable spending around $2000 plus or minus. 

Any suggestions?  I live in the SE corner of Washington State and would gladly pm my telephone number if you'd like to call and walk me through some ideas.

Thanks in advance,

Bob