Integrated or speakers

I always start upgrading speakers..then look for a nice match for them.

As I always like to say - if you don't like the sound of your speakers, you won't like the sound of anything else in your system.

Well said Learsfool, something like; garbage in, garbage out. Also agree that amp and speakers need to match. Good speakers can sound poor with the wrong amp.

All this advice and no one asked what his system is, unless I'm missing something.

What's the current system - source(s), amplification, and speakers? Are the speakers set up/placed correctly? Is the room treated? The system is only as good as the weakest link, and that includes set up and room acoustics.

It may be a case that your speakers aren't placed properly/optimally. My speakers sound pretty different moved closer together or further apart, closer to or further from the back wall and corners, toed in or out, and so on. It's not a subtle difference either.

Or it could be a case where your amp isn't strong enough to properly drive your speakers.

People suggest speakers first, and it makes a ton of sense. Some suggest source first, and that makes a ton of sense too. I think the best advice has been given - hear combinations of stuff, find one you like, and look to upgrade to that. If you go that way, it'll be irrelevant which you buy first, so long as you're not underpowering the speakers if you buy them first.

But before spending a dime, make sure you've exhausted all your free options. No point in spending money if you don't need to IMO.

My current system:

Yamaha A–500 Integrated (I think it’s from the 80’s?)

Rega p1 TT

Toshiba CDP with modifications by Response Audio. This thing is just amazing.

Dynaco A-25 Speakers with SEAS Prestige tweeters

DIY speaker stands

This system does a nice job but the speakers and amp are limited.