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OK, Koyo back on the list!

The upper hose neck on your radiator has a hairline crack it's normal on the turbo Subarus around this age. The one on my 2002 WRX let go about five years ago. I replaced it with a Koyo all-aluminum Hyper Core. Perfect fit, fan mounting hardware included and not too expensive if you grab one on sale or from a company with deals ongoing and free shipping. Rallysportdirect.com has free shipping on orders over $200, I bought the BRZ Koyo rad for the RX-RA from MAPerformance.com. I would just look up the part number and search for it on Google Shopping, see who has it cheapest.

It's fairly common for radiators to leak, usually the plastic cracks. This wouldn't be surprising at all. I hate to guess without seeing it in person, but this is by far the most likely scenario. Radiator shops, if available, can test them for leakage. You could try pulling the radiator, closing off the top radiator hose inlet/outlets, turning it upside down and filling it with water to see if you can find the leak. But it may not leak without heat/pressure. Or try the UV light kits/technique, but I've never done that. I've installed probably 10-15 $100 new radiators from various sources and never had issues. If another 15 years of ownership is likely a new Subaru OEM radiator probably makes sense. I'd prefer Subaru hoses.

Once you install OB struts then you can also install larger wheels/tires for more lift. You can gain another 1" from tires.

Yes. New 05-09 outback struts and springs and install them using your legacy hardware. Some people prefer 00-04 outback struts as they’re better and last longer. If you go that route you’d install 00-04 struts with 05-09 outback springs using your original legacy top hat and hardware. for used you can Bolt on complete 00-04 or 05-09 outback strut assemblies and you’re done. This will net you roughly 2-3”. you can also retain your legacy springs, top hats and hardware and install just 00-04 or 05-09 outback struts. That would be the minimalist cost with new struts instead of used ones. This will net you roughly 1”-1.5” 05-09 struts are so weak and consistently fail at lower mileages than other outbacks/legacy’s that id definitely want new struts if I’m swapping 05-09s at all. Forester, I’m unsure. you can use 2008 and earlier front strut assemblies but I don’t think you can use the rears.

Fooled around a little more last night and found another area that was covered up by a previous repair. The front fender was replaced at some point due to an accident. Looks like they just tried to pull some of the smashed area out then covered it with bondo. Some had fallen out, it was about a 1/4 inch thick.