Seeking Advice to Improve My Audio System ($1000 Budget)

If you're unsatisfied with the sound your system is providing, yes speakers would be the most significant upgrade.

Do you live in an area with audio dealers or with a solid craigslist / FB marketplace?  If you really want to stay under $1000 and get the best possible bang for your buck, I'd highly recommend trying to find some used active speakers that are in your price range.  The Focal CMS range are professional monitors but will accept an XLR or RCA input and will blow away your current speakers.  I see them going for like $700 a pair for CMS 65s, the larger ones.  These things will absolutely crush your current setup and if you boost the bass, they actually hit below 40 hz pretty solidly.  

Otherwise, some used active KEFs (meta wireless) or other actives could be a straight steal for you.

Then buy a wiim ultra for around $300 and you suddenly have come into the 21st century with a solid streamer and super solid speakers.

Best of luck OP!  Don't think you need to spend insane money to get good sound.  You just have to open up your search to used, or find local dealers that can give you solid discounts and trial periods on gear.  Don't just buy something off the internet because people say it's good.  Test it in your room on your system!!!

$1000 only these days.....??

Step a) Your current speaker is terrible/terrifying. Move it into the garage or deck for casual listening with bluetooth or something.

Step b) Get a pair of these Tekton Lore Ref speakers for $810.  It is a 96db sensitive speaker with some good extension, clarity, midrange, etc. You will understand it better when you start listening to it.

https://tektondesign.com/product/full-range-speakers/mid-towers/lore-reference/#color

Step c) Get this fosi audio za3 amp for $150. Plug your cd player and turntable into it.

https://fosiaudio.com/products/fosi-audio-za3-balanced-dual-mode-class-d-amplifier?variant=45459725746406

Sum total  = $960,  

Step d) When you have a bit more cash later, get this subwoofer from verafi audio, verafi caldera 10 subwoofer for $200. Plug it into the sub-out of the fosi amp...and move it around in the room, till it clicks in place sonically.

https://verafiaudiollc.com/products/vanguard-caldera-10-active-subwoofer?srsltid=AfmBOoos2uSKrycUMjpCKWG4aC37eZV3TuJpbiId_ggTCe79Odi66xEV

Sum total = $1160

Above mentioned steps should make your music a lot more enjoyable.

I want my next investment to be around the $1000 range, but am not sure where to go with it. 

(Not sure if you can see this if you're not a member of the Audiophile Foundation)

We had a recent "$2000 Budget System Design Challenge", and the results may be seen at: https://sfaf.clubexpress.com/content.aspx?page_id=5&club_id=794405&item_id=115420&

The rules were pretty loose, but they generally all include at least 1 source component, so the amp & speaker combos are at least in the kilobuck neighborhood.

You might also consider something like the Parasound NewClassic 200 Integrated Amplifier; they've got a couple used ones at $599 at The Music Room (NOT to be confused with the  Parasound NewClassic 200 Preamplifier).  They just slid a 110 watt/channel class D amp into the 200 Pre case, so you get a full-featured preamp (MM/MC phono, DAC, subwoofer support, HT bypass, remote control, preamp out) plus power.  That gives you plenty of flexibility, and you can bypass any function later with a better external unit if you choose.  The current Parasound model is called the NC200INT, new at $899.  The company was sold a couple years back, so I think this is mostly just a re-badging.  Of course, you'd need to buy a pair of speakers, too!

BTW, speakers are the most important issue.  While I love the LS50s, I personally would never use them without subwoofing.  Since I'm reluctant to get a subwoofer, I've always ended up with floor standers.  Are your speakers currently on shelves, desktop, or stands?  Are you willing to dedicate some floor space to them (whether towers or smaller speakers on stands)?

it’s tricky because if you go to passive speakers, you would need an amp. 

You can get a decent vintage receiver for under a $100, on ebay, craigslist or shopgoodwill. I would go with Denon or Yamaha. You can’t really go wrong with it. But you can add Onkyo, Adcom and NAD to the list too. 

For speakers, again no need to spend a $1000. There are a lot of vintage speakers that sound great. Cambridge Soundworks, Celestion, Boston Acoustics, Monitor Audio, Paradigm, etc. The key is to find quality and avoid junk. 

People here spend many 1000s a year on cable upgrade alone. They can’t really make meaningful suggestions for a system that has no quality component (maybe your CD player is OK) especially the Rega 1 is despicable. I am saying this as a Rega fan, that version should not exists. 

(I am terrified by the Wavetouch Audio WT-95 idea that would "take" your $1000 and would leave with you where you are right now. And coincidentally, the person suggesting it is the person selling it. Ouch. No.)

You can get great sound from vintage, quality components. Just do your research or feel free to pick our brains. Knowledge substitutes a lot of $$$ in audio. 

Re KEF and Hegel - no, not a good idea. Unless your goal is to spend many thousands and be done with it. The LS50 has a very unique sound, needs very tricky placement, and on the bright and overly detailed side. Which is exactly what the Hegel does, too much separation, too little warmth and fluidity. Together: bright, fatiguing, in your face notes, that feels like a cat scratching your side burns. Both the Hegel and the KEF are impressive and good value for the money. But you need to find out if your ear likes that type of very revealing, analytical, monitor sound.