Largest Impact - Arm or Cart?

Of my 30 years of experimenting, i think the cartridge.

I agree with Jaybo.

I've got an Incognito-wired Rega RB250 arm with Michell Tecnoweight and Tecno VTA adjuster and it sounds great with the Benz Reference 3. That said, I would trade you for your OL Encounter and Benz M2...

Your system doesn't show a Record Cleaner...so I would vote for a record cleaner first and then you might consider the magnetic bearing upgrade for your Clearaudio Table.

I'm not sure you're going to get a big upgrade from the Origin for $1K. Perhaps a used Graham?

However, you could get a BIG sonic upgrade by moving to a better cartridge. There are plenty of candidates at $1K, but I'd personally buy one new rather than used.