Advice on Speaker upgrade vs System Component Upgrade

I have seen your Room Dimensions and a proportion of your Rooms Layout.

I would not be too hasty to focus on controlling Bass Energy, the Deep Pile Carpet is already absorbing energy from the lower frequencies.

I feel based on my own experience of working in a smaller space that working with the energy in the room and diffusing it, can prove to be the best starting place.

Hearing Sound that is not a reflected sound can be appealing with immediacy.

How the sound is managed is a evolving experience, more can be attained as the ear learns more of what is an attraction.     

square rooms are difficult

So thanks again for all the help - what a great community!

I have been leaning Sonus Faber for a long time now, and thanks @skchun for pointing me at the Guarneri Evolutions on TMR - i had a think, and for that price point, I decided to pull the trigger.

Beautiful speakers, and I love that SF sound. They are well reviewed, and should be a next step up in quality... or at the very least a different sonic character to the Dynaudios that i know that i love. They also apparently sound good at low listening levels which is important to me as i do most listening late night. Finally, if they don't work out, they will have definite resale/trade in value, or could sell the HS (but i love them and won't sell unless i have a very good reason) 

They should work in my small room better than a floor stander (i'm just not convinced I can ever make that work in my room really well). I have an old pair of B&W CM10 S2's that i had in there and had trouble with bass - I certainly preferred the HS + Sub as i could keep the bass levels down at night, though the HS are a better speaker all around so not really fair.

These will also benefit from the treatment i'm going to do (gik acoustic or auralex). Again I don't really have a "boomy" room with the carpet, curtains and closet in the office room, so i'll start with some diffusers on side wall and behind listening position and go from there.

I'll be able to directly compare them to my Heritage Specials and see which i prefer in the room. I also think that I will have the option to move them to the living room if that's where they end up sounding best, but I won't be in a hurry to do that - they will get way more use in my office/listening room.

I'm pretty sure that the next purchase would be a good tube amp with more grunt and quality than my Wilsenton R8 (nice as that is for the price)... So i'll throw that bone out there to the group...

I'm also pretty sure i'll add a second sub for the stereo pair at some point. 

Thanks again for the support and advice - very much appreciated!

Happy Listening!

Congrats!  Keep us posted on your impressions of you could. 

@gmdodd , In regards to room treatment there are really two issues, evening out bass response and helping the system produce the best image.

Bass traps are worthless. If you have a bad room for bass the only two options that really work are multiple subwoofers and digital room control. If you do not want to get involved with all this stuff the best solution is to move your listening position backwards or forwards until you find the bass acceptable by ear. You might only have to move it a foot or two.   

Improving your image and dampening out artifacts like sibilance requires muting first reflection points throughout the room. This can be done with expensive panels from various companies but also just as effective is really cheap 4" acoustic foam tile. You could probably treat the whole room for less than $100.00! That is what I use but in my case the speakers hide the tile.  As for whether or not the foam tile are aesthetically acceptable is a matter of personal taste.