@justinrphillips I'm in the same boat as you in terms of finding something better than what I have but as speakers are more obscure or get older, it's hard to find comparisons with what is currently available.
For example, I went to go a local audio store to test out the Proac D2Rs which seem to be really great speakers. While they sounded pretty good in the treated audio room with a decent front end, they still did not beat the SB Acoustic Ara that I've been using over the past year. It's possible that the synergy is much better in my system or it could just be that the value of DIY is 2-3x.
If you're looking for something interesting and good value for the money, I'd recommend something DIY or from a smaller company like the Fritz or SB Acoustics or BMR, etc. Those are gonna be great and within your budget. I'm willing to bet that an SB Acoustics ARA at the current discounted price will run circles around an LS50.