A small space can be problematic, like Yuri points out, maybe bigger speakers or sub won't make a huge improvement. Depending, it could create mud instead - unless applied very subtly maybe.. but so many factors need to be seen/heard, like shape of space, reflective surfaces or opposite etc.
Really hard to say what would be good to try without experiencing the space
Your gear looks OK (unless really not liking something) - but to just improve the space, maybe some really simple things can help.. like hanging a drape on the walls in front and behind you when seated. In a tiny room, this may remove rebounding sound and can improve things significantly (can be a big bang for very few bucks). Heavier the drapes the more damping can happen - in case your room amps up muddy low-mids not just early reflective slapping etc.
You could put your noisy laptop to the side, behind a baffle (or couch etc.) and run wires or Bluetooth portable PC keyboard and mouse and an extra monitor over HDMI.. no need to have our PC next to us - put it in the next room if you want this way. Also very inexpensive.
Maybe have your 'normal' PC working desk on your left with laptop under desk behind a baffle + your dpiano keyboard and extra monitor and qwerty/mouse and monitors on an L angle.. that way, you might fit a monster slab keyboard of choice in - not just all front-facing.. I do this in my space, not to save room - but because I want my PC work to be separate from my playing space.. even if it's just a few metres away, it's like a holiday to load up Pianoteq and go sit at the piano - monitor on or off depending on if I'm recording or hopping around between presets or just playing/practicing with 1 preset.
Build a ropes & pulley contraption which lowers your keyboard down from the ceiling - or cut a hole in the floor and build an elevating platform which rises the keyboard up like the organs in a theatre Kind of joking about solving the big keyboard dilema
Probably best as said elsewhere, let these things breath for while, build the budget and in enough months you'll probably move on to the thing which stands out most to you.. keyboard, speakers etc.
Like any recommended speakers or keyboard, you really have to test for yourself IMO.. if relying on WOM or web forum, follow up by more research at minimum. I like new companies sometimes but the old makes are used in professional studios etc. for good reasons. But, if you don't intend to mix or produce your piano sound, but rather play like in player position with less regard to a DAW, then maybe an upgraded to 8inch speakers might be better than adding on a sub woofer? My general perception is that 8inch cabs would be my bare minimum for suspension of disbelief for any music.. 5 inch and less are "making do" or budget to be honest, but your brief here is "How might I spend about 1000 clams?" If spending more, there would be even more interesting options of course.
I'd probably be thinking, if more-or-less happy with things, that a next gen type jump in the whole experience might come with getting a good DAW and plugin setup. I've been experiencing a large increase in the quality of digital plugins in the last decade or so, such that I no longer pine for something like my 70s era desk experience. My first job was in a studio co-running a 48 channel desk - I feel I can do anything now in my DAWs with the various plugins which mimick the rack effects of the old days - and importantly also plugins which work for modern release rates etc.. some good $s could be sunk into that side of things, esp. if you want to record your music.
Headphones - unless unhappy, they could be fine. Like above, if you have a DAW and put a plugin like Waves Abbey Road Studio 3 on, you can help the whole earphone experience, no matter the brands of cans. I, and earlier tech like it have really made working in headphones for any length of time a rational expenditure of human energy
Just some thoughts - hoping you get things just the way you want them - and also wishing a happy birthday and maybe most important of all, well done! and hat tip for the nocturne! I feel the sense of achievement in your posting - and 100% it's one of the most wonderful things in our world as musicians - keep enjoying the magic of it keybender!, Cheers.
Pianoteq Studio Bundle (Pro plus all instruments) - Kawai MP11 digital piano - Yamaha HS8 monitors