What would you upgrade?

Hello, fellow audio enthusiasts. I'd like to get some opinions on what your next move would be if you had the following gear:

Signal Path:

MacBook Pro > DacMagic Plus > Dared Sl2000a or Bravo Audio Ocean v2 > Peachtree Decco 65 (pre mode) > Emotiva UPA-200 > Focal SW800 Sub > Focal 807VW or Totem Rainmakers

Clearly a lot of room for improvement here. Where would you start and what would be the reason?

Nothing is untouchable except the MacBook Pro.

Like the idea of towers/monoblocks.

$5000 budget for upgrades.

Thank you for any suggestions you can provide!
Thanks, Paul.

I'm noticing a trend here. Everyone is very emphatic about the source. Perhaps I will give HDtracks another go. Maybe my system with turn into something completely different then I've been used to. Only drawback is there is significantly less content available at this point.

I do like the "buy the best you can afford" idea instead do spreading thin, though. Maybe 1 major upgrade every 3-5 years.
I would fix the music while you look at the components. Mp3s dont sound good in any system.
What stands out to me is the relationship between speakers and your unusually high ceilings. The proper synergy here will do more for your overall presentation goal than any electronics choices you may be considering.

I would seek a professional suggestion as to possible speaker directions. At the very least go to speaker specific forums and clearly describe your room. Give your budget as twice what your willing to spend and consider those suggestions on the used market.

What your looking for is a more specific type of speaker such as, high efficiency, horn, open baffle, panel, etc.. Don't leave out your using a subwoofer. A clear direction here will determine any future electronics upgrades.

I just heard Kipod server/streamer feeding a Direct Stream DAC and it left me thinking that Hi-Rez media clearly isn't the total digital solution. Getting the most from ones collection of 16/41 recordings is far more important than rebuying a library into Hi-Rez.

I'm not a digital vs analog user, I'm into the music. So if it's not on an LP, no worries, the selection of affordable and listenable digital sources continues to grow. Source selection, digital or analog, is a very personal consideration. IMO, Ted Smith's work on the Digital Stream is as dramatic as Gordon Rankin's was on USB. Fortunately for me, my LP collection is much larger than my digital.

If you're considering LP playback, advancements in cartridge setup, especially in rake angle and azimuth adjustments can be more important than the money spent on the hardware. Complete tonearm adjustability is very important.
M-dab, I like the idea about speaker specific forums. I should take some photos and get some suggestions on how I could best handle the room situation. I can also use the loft upstairs and take care of a lot do the issue I face setting up downstairs, however, that's a much smaller room with quite low ceilings. Worth getting opinions for sure.

I ended up demoing the 1028BE's today and really enjoyed them. It looks like I'll be able to get great trade value on both sets of speakers and the sub so I think I'll be pulling the trigger on them this week. I think they'd overpower the loft so downstairs might be the only option.

I'll be bringing the Peachtree/MacBook Pro in to demo with the Focals. Should he interesting too see how they play together.