Upgrade thoughts and reccomendations

I'm trying to decide where to upgrade next.
Thoughts are a new amp and speakers
What I would like is a sound that opens up the dynamics at a lower volume and where the speakers really disappear
I like the sound of my system - it does sound good - and often very good - but I live in a condo and when my daughter gets off the train late at night, opens the door and says: DAD I can hear Miles Davis down the street....LOL...I need to change something
Amps? where to head for a real upgrade?
Speakers? I'm been researching Dyna Audio but don't know enough
A little history
At the beginning of the year, without any warning and not even on my radar, I put together a system. It started with a pair of B&W 305's a friend was selling. They spent a month or two hooked up to 1970's JVC college gear and an old Dual deck/ Shure cart.
Then I bought some other things.....
My current system is as follows:
Rogue CM1
EAR 834P MM/MC phono stage
Nottingham 294 Space Deck and 12" Anna Arm
Lyra Delos Cart
Totem Hawk Speakers
It fairly sings
I won't mention the digital side - it's decent but all up for a massive upgrade.
Thanks for any reccomendations
1. Budget?
2. Room size?
3. Type of music you prefer?
4. New or used?
5. Stand mount or floorstander?
1. $5000
2. 14' x 28'
3. jazz, classical, occasional rock
4. used
5. thinking stand mount but open to another set of floorstanders
Condo electrical can be less than good for audio. That's the place to start. Ive owned quite few PLCs over the decades

I highly recommend  Core Power conditioner and Deep Core
Once they are broken in and your ears acclimated, then come back
The Harbeth 30.1 would be a nice fit. You can get them used well below 5 grand. I’ve owned them but they didn’t work out in my smaller room so I went with the smaller P3. My friend just bought a pair and loves them.
Here is a review!
I'm not sure why changing your speakers or your amp is going to affect the amount of sound that can be heard out in the street. You could buy more efficient speakers that sound better at low volume. Is this what you mean?

Ozzy maybe yes more efficient might work
Hilde I like the Hawks. They often surprise me
You could buy an excellent headphone rig for $5k and play music as loud as you want.  
As for Dynaudio speakers (keep in mind speakers are a very relative thing) I discovered long ago that was the sound for me. I have auditioned/owned so many over the years but once I heard that sweet Dynaudio sound I knew immediately that was it. I also have DALI and Monitor Audio in a smaller bedroom and living room setup and they are also great speakers but for me nothing can reproduce the detail and soundstage of the Dynaudio's. With that said although they sound great at lower volumes I really find to get the best out of them they love power and volume. In fact honestly that was the driving force in selling my condo and buying a home, because I just needed to be able to put the pedal to the floor and let the Danes open up and fill the entire place with that magical sound of theirs :)

I currently have Dynaudio Evoke 50's, 25C and 10's being driven by a Simaudio HT200 5 channel Titan amp and for me it can't get any better...
Pointless post.  That's why so few posts.

Your whole system is up for grabs or any part of it.
We have no idea what kind of sound you like.
If I think the Bigwatt is a wonderful amp, what use is it to you to know that?

your system is fine, very decent choice of gear, in decent balance and proportion

headphones for loud late night listening is a good idea, otherwise don’t change anything if you like what you are hearing

that been said, if you are really wanting a ’massive upgrade’ -- are you prepared to spend a massive amount of additional $ to achieve it?
If you start with the power conditioning, regeneration or switch to DC
and ensure the room is well treated you may find the improvement so
great you need no new gear based on your list.

Keep us posted please.
Try an amplifier with loudness switch and or tone controls to bring up some of the frequencies at lower volume levels. 
Thanks for the responses. Since posting this I've been "rearranging" furniture and positioning of speakers. Noticeable differences. I think I'll focus on this for now. Looking for a an area rug for hardwood floors
You could also try adding a subwoofer. That may be the most inexpensive way. You’ll be surprised how it can expand the soundstage especially at lower listening levels. I use two and I was truly amazed how they opened up the sound stage at all volume levels. Good luck! 
Hey there 

I would try some Maggies with SUB.
If your budget permits highly recommend high current SS. amp pre owned 
Jeff rowland 125 2ch.

You will not be disappointed