It's a conundrum I've suffered with a few times, and I've always sided towards the cheaper option.
Right now it's this - I'm seriously considering replacing our long suffering '08 Mazda 3 with a 3rd gen Outback 3.0R. We're in Peru (the country, not the town), things here are different. Cars are worth more, lives are worth less, roads are variable, and if you want anything done how you want it it's best to do it yourself.
The 'family' car is an LR3. It's done better than expected, but it's getting tired, and my confidence in it is getting ever lower. SWMBO hates the Mazda (it's too small/uncomfy/cheap/tin can depending on her mood), and so it's a battle to use it on family trips. It would be good to have something a bit bigger, safer, dare I say it comfier to not have to use the LR3 on long trips. Personally I was leaning towards E39s (as per my various threads), but German plastics/electrics after 25 years here may not be the best combination. My preference is RWD > AWD > FWD (low speed, low grip surfaces here). I was looking at H6 Legacys, but the ground clearance for here isn't great (I run Mazda 5 springs on my 3), and there's not that much more space compared to the Mazda. I'm not that keen on having 2 SUVs in the family (although not dead set against it yet and do have some high mileage 3rd Gen 4runners saved in Marketplace). The H6 Outback seemed like a reasonable compromise.
So, there are 2 for sale (in all of Peru, and the only ones I've seen in the last 5 years). Both 2007 model year (so the facelift/SI Drive etc), both 5EAT. One is unloved, and is $7000 (will probably come down $500) and has been for sale for a few months. Dash is cracked, aftermarket head unit with horrible install, overall dirty, missing headlamp washer, bad paint, has had an "injector service" (yikes), ABS light on, something non-standard in the rear exhaust (no passenger tail pipe visible). The last 3 years of inspections show it has been up and down the country and out in the provinces a bit, could mean it's reliable, could mean it's beat to hell
The other one appears (I've not been to look in person) to be a cared for version, and is up for just under $9000 (for reference there are 2 reasonable H6 Legacys, one at $9000, one at $9500). Owner seems to like Subarus judging by his social media..
Obviously the $9k option is much nicer, but $2k buys a lot of parts. The only thing it couldn't easily fix is the dash. The cheap one has 150k kms, the more expensive 125k kms.
The cheaper one could be bought as soon as the Mazda is sold, and bits replaced depending on how critical. The more expensive one would need some financial juggling/using some finances that were assigned for other stuff.
There's nothing actually wrong with the Mazda (well a snapped rear swaybar endlink aside which means it's got the stock rear bar on for the minute), it's just a desire to change...