Note the stops in my OP: Oregon, N. Cal., Colorado, TX. Many points along the routes to these stops typically feature moderate temps in winter months. Besides, we Wisconsinites - albeit fairly recent transplants - are supposed to be cold-weather immune 
(still working on that part. . .). Anyway, doing the chuckwagon thing would be weather-permitting.
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That struck me as well. At minimum you’d want a teardrop trailer with a galley like @Whitey suggested. Realistically since it’s in winter, you want a small motor home with a cold weather package if you’re planning on using your vehicle as your kitchen. (The cold weather package is to keep the plumbing from bursting in sub-zero weather)
Didn’t the Rav 4 offer a 4WD configuration in the early 2000’s?
Almost positive they didn’t. Maybe the 4Runner?
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Wikipedia’s nomenclature may be inconsistent, don’t know, but it’s description of the various generations of Rav seems to imply 4WD was available up to around 2011.
It may have been called 4WD or 4x4, but it’s nothing like the 4x4 system on a Suburban or full sized pickup. They started with a FWD and added on the rear drive system. I don’t see how it would be any different than all the other systems that are FWD-based.
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The line between 4wd and AWD has gotten real fuzzy over the years. I still believe there is a distinction though. Current RAV4’s are truly AWD or FWD. You don’t shift into 4wd. It’s always on.
Older RAV4’s you did shift into 4wd, but there wasn’t a low gear range.
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A very confusing situation. Here’s more than most want to know:
From what I see both the 2000 (termed “4WD”) & 2018 (termed “AWD”) Rav 4 appear to have a part they call a “transfer case”, the main parts being a pinion & ring gear, a little hard to decipher from the drawings what it does exactly, but I’m guessing it operates like a “proper” center differential to transfer the transmission output power to both the rear wheels and the front wheels, while allowing the front/rear wheels to rotate at different rpms as required. No xfer case selectable gear-range selection though. The 2000 model looks to have the capability to shift from 2WD to 4WD mode, there’s shift fork in the transfer case ass’y, but I don’t see that function in the 2018.
I do not know the specifics, we have a 2017 rav4 awd, it works fine in the snow, downside 5k mile tire rotation, still wondering what happens if you use the full size spare. 
Isn’t that normal for most tires on any vehicle. That is what is free at Discount Tire for our FWD vehicles.
I don’t think the OP has any use for an old 4WD Rav4, he currently has a 2016 Subaru Outback.
We had a 2003 Chevy Trailblazer which we used to pull a 19 foot travel trailer It was comfortable and up to the task. They were made from 1999 to 2009. The GMC Envoy is the same vehicle made by the GMC division of General Motors.
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Sounds good! Also a possibility would be to rent a class C motor home. Not too long and very comfortable. Just have to watch out for the frozen pipes.
In addition to watching out for frozen pipes, you’d want to either tow a car to bring with you or plan your trip carefully to make sure you always have adequate parking and space to maneuver.
A class B motor home would give you less space but more flexibility.
… and at Costco–and possibly other venues.