Largest Impact - Arm or Cart?

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.

Selling your Origin nets you under $1000. Add your available $1000 and you can't make a significant upgrade.

You're in the same situation with the cartridge.

If it were me, I would save more money and buy a used killer tonearm.

A great tonearm with an average cartridge will outperform an average tonearm with a great cartridge all day long.

IMO of course.

I spent on a killer cartridge. I consider it money well spent. BUT the arm must be of reasonable quality: correct static and inertial mass, very easy motions around pivot(s). It becomes a bit of a black art. Example: I was strongly dissuaded from mounting a Helikon on a Dual. This from a guy who sells Helikons. (Helika?)
cheers apo