I've only skimmed through this thread, but it looks like you've gotten a ton of great advice. I'll offer my story, since there's a lot of overlap with what your situation.
I live in Oregon as well, near Astoria. No local Nissan or EV dealerships here, so all of our shopping was online and in Portland. Platt Auto Group in Portland is fantastic, they specialize in EVs and have a wide selection of Leafs. I somewhat regret that we didn't buy from them, but I wanted a CPO warranty, which you can only get from a Nissan dealer. We ended up buying through a Nissan dealership in Portland (Carr Nissan). It was an awful experience, but we ended up getting a great deal.
We bought a 2015 Nissan Leaf SV with ~25k miles & 12 bars for $11,500 off the lot. We financed it to get a $700 incentive they were offering, then paid if off within a few weeks (then the Nissan bank lost our title and we had to use a temporary moving permit for 6 months, which was annoying but actually saved us 6 month's worth of car registration). We should be getting the $2500 Energy Trust rebate check soon, that will bring our final price down to about $9000. If you plan to get that, you'll have to buy pretty soon, as that program is first-come first-served. Our car was off-lease and in perfect condition. I didn't know about LeafSpy at the time, but I did get the battery report, carfax, etc. before buying.
We have one kid in a car seat, and frequently drive around our friend's kid in a booster seat. 2 adults up front and 2 kids in the back is no problem. Trying to cram a 3rd adult in the middle seat between two car seats isn't comfortable, but it is do-able for a svelte adult on a short trip. 3 car seats abreast won't fit. Cargo space is fine for diaper bag, groceries, backpacks, generally everything we need. As you probably already know, these older Leafs are not meant for road trips. Ours has Level 3 Quick Charge capability, which I'm definitely glad we have, since not only do we need to quick charge to get to the dealership in Portland for service, but it greatly expands the range of day trips we can take in the vehicle. Through trial and error, I've learned to only plan trips that require no more than 1 quick charge stop whenever possible. We have an ICE SUV (2008 RAV4) as a secondary car that gets driven about once a month, and for longer road trips. We spend about $20-$30 per month on gas for the occasional driving the ICE car gets. I expect you'll do about the same, though your Outback probably gets better mileage.
As others have said, the Leaf makes a great primary vehicle, and your Outback will make a great secondary vehicle. If you do go this route, the niceties of the SV or SL trim level are worth it. We don't like leather seats, so the SV is perfect. I love the cloth seats, very comfortable. Also love the heated steering wheel and heated seats. In the Oregon winter, it is much more economical to use these two low-power heaters to heat your body instead of trying to heat the whole cabin. It is still nice to have the heat pump to preheat the car, but we rarely use it while driving. My only gripe is that my feet will get a bit cold sometimes. Running the defroster is necessary as well, as the front window will fog up, and if you manually disable the AC/Heat options that turn on each time, you'll save some power. It is annoying that there's no built-in fan-only defroster mode, but I guess Nissan thought that folks wouldn't like blasts of cold winter air blowing on them just to save a few watts...silly Nissan.
My other gripe is that the bluetooth system doesn't handle multiple phones well. Pairing one phone is perfect, but when you pair a second phone it rarely works, or you have to manually disable the first phone's bluetooth and fiddle with it...just annoying. Drove me to put a bunch of music on a USB drive, so I can use that and my partner can use bluetooth. Also the built-in NAV is pretty bad since it is now 4 years out of date, I just use Google Maps/Android Auto on my phone connected to a magnetic vent mount. Plugshare is the best app for finding chargers in the wild, and for trip planning. Oh, and be prepared to be harangued by Siruis XM radio adverts by phone and mail for the rest of your life...I'm still trying to figure out how to get them to stop pestering me...I seriously don't want Sirius!
I do wish we had the 80% charge limit option, and I try to manage this manually with the car's built-in charging timers. It would be much nicer to just be able to plug it in and not think about it. Still, that's just because I'm trying to get about 10 years out of this car, if you charge it to 100% every night you might shave a year or two off the battery's lifespan (same goes for the Li-Ion batteries in your phone and laptop).
We use Level 1, 120V charging at home, and typically charge for 6 hrs per night in the summer and 8 hrs per night in the winter, and only when needed. We've come up with a system where we only plug in the car if the battery is below 50%, and we try to unplug it around 80%. I'll probably install a 240V circuit for Level 2 charging at some point, but it isn't really needed right now, it will be more important if we ever get a second EV.
The Nissan app rarely works from our home, since AT&T coverage is awful around here (the car uses AT&T's 3G network to communicate with the Nissan servers, which in turn communicate with your phone app). In Astoria, Portland, and pretty much everywhere else I've tried it the app works fine, and it is very nice to have when relying on public chargers.
In all of my research since buying the car, I've come to the conclusion that the 2015 model is the sweet spot of all of them currently available on the used market. It has the best version/chemistry of the 24 kwh batteries, quick charge, nice heating options, etc. And the price is unbeatable, at least for now.
As a closing note, you'll be amazing at how much money a used Leaf will save you. You should be able to find one for a low purchase price, like we did, and the fuel costs are incredibly low. We just did the math for last month, and we spent about $22 for all of our Leaf driving while charging exclusively at home (total of 808 miles, according to the app). If we had driven those sames miles on our ICE car, it would have cost about $100 in gas. Once our solar panels are installed in the next month or two, our driving will basically be free. Maintenance is practically non-existent - outside of the routine dealer service checks (same as any ICE car), all you have to do is top off the windshield washer fluid, top off the tire pressure (LeafSpyPro monitors this for you), and rotate the tires every 5k miles (which is more often than an ICE car). I also love how clean my garage is with an EV! No oil marks or grease anywhere.
Like you, I tend to be verbose, especially when starting a new thread, and I wanted to mention that I appreciate the clean formatting in your original post, makes it welcoming to read. I don't check these forums too often, so feel free to PM me if you have any specific questions for me. Best of luck and happy shopping!
2015 Leaf SV, 25k miles, 12 bars