Ser_egg, your oil leak at the filter is at the head gasket. It leaks oil down onto the oil filter. You’ll have the same oil leak on the rear of the passenger’s head.
“Back in the day” you were given 28 days to rectify any RW issues and return for the follow up inspection. 7 days is an absolute push and a pain in the arse most of the time, namely if you’ve got things to tick off the list.
If/when you get the head gaskets done use the multi layered steel head gaskets. I’d have to dig up the part numbers for you to use. If you use the ones listed as per your VIN, you’ll most likely have the same leaks within 100,000km. My sister’s liberty is testimate to this. 330,000 - replaces the head gaskets on her EJ251 to pass road worthy due to the dreaded HG oil leak. Used the vehicle’s VIN to get the “correct” head gaskets. Bad move - seems Subaru don’t acknowledge this issue and haven’t change part numbers as a result.
You could try steam cleaning the area, then wipe down with metho and push the sealant into where the oil was leaking from the bottom of the head gasket. If it’s coolant leaking, you’re up for a HG job to get rid of that problem - and for your RWC.
I’m currently working through my mother inlaw’s “new” SG. Engine leaking oil like a sieve - namely from the head gaskets. It has 370,000km on the clock but still pulls like a freight train. I’ve put four times the amount that we paid for the vehicle into the sorting of the engine with the aim to not touch it for a long time to come! Other than that, the rear struts needed replacing and it should be good for RWC. The amount in the engine work is parts only - all genuine. I realise DIY isn’t for everyone, so consider labour costs too.
RWC isn’t always “fun” since it can come down to who’s doing the check. It’s kind of like gambling to a degree. Some RWC mechanics take it to the n’th letter of the book, some will let certain things slide.
Eg - sister’s liberty. Went to one place, got a list as long as my arm - including needing new fan belts due to cracks!! They noted suspension bushes needed replacing and a couple of other odd things. Went to another place near my folks, found a hole in the exhaust, they welded it, car passed its RWC check. 6 months later we replaced all bushes and the front struts. The irony of the weld job is that they cut another hole in the exhaust removing the heat shields...
All the best with it! It’s a gamble at the end of the day. Either get the work done now or get it passed and have down time on the vehicle later... your call.
Cheers
Bennie