I bought my SR5 4x4 out of West Palm Beach FL and had it shipped up to Wilmington NC. Had like 55,000 miles on it, was a trade-in at an Audi dealership. They had it on Ebay.
Smelled a bit like Guido the killer pimp when I got it, but has been a great car and now is at almost 150,000 miles.
If you can wait that might let the market calm a bit and you could get what might feel like a better deal. If I could do it again I'd have held out for one with a backup camera and 3rd row seat. Kids/ kids friends... but the wife's Highlander has all that and more (XLE trim).
Pearl white and super white have paint issues (some do). There's a recall available to some.
Refresh was 2014+ if that appeals to you. If you run across a 2010-2013 Shoreline Blue Trail grab it! I had the chance to get one and balked, gone.

I should have mentioned up front that my urgency is based on the fact that my 20/20 Outback has only 19,000 miles on it, but the 3-year warranty is up starting December. So I'm thinking 5 months of warranty coverage is worth something to a buyer, which makes me not want to wait to see if the market changes.

When I purchased my previous car new, my strategy was simple: research, find best advertised price, ask dealer if they can beat it, went with dealer that beat it by plenty. Given that price breaks seem doubtful right now, I'm thinking w/my trade-in situation (act now, capitalize on June-Nov. warranty coverage), maybe I just look for the dealer that gives me the best trade-in value? Presumed wisdom is generally not to mention a trade-in till you get your best price, THEN bring up the trade-in.....but maybe that's not as applicable here, and would considerably simplify my search/dealings/etc. Thoughts?

overthinking the process, the warranty doesn't make much of a difference. Find the color & model you want , search within a radius you are willing to travel. Basically if at MSRP or lower its a good buy now with the market, capitalize on your trade. Consider carmax , and others to have a better idea as a base TIV.

“Surprising” the dealer with the trade after you’ve negotiated a price for the new vehicle just means they’ll give you less for the trade. You’re not getting something for nothing

sell OB to carmax, take the check and buy a 4runner.

We picked up our SR5P right as prices were starting to climb on some vehicles, but not all of them. We wanted to go the straight dealer trade route, but my wife decided to at least give CarMax, Edmunds, Carvana and a few other of the online places a shot. Prices offered on her Jeep Cherokee were much higher at all of the online places than the dealer. Two dealers had offered us $5400 and $6k. I'm pretty sure Edmunds had the best price of the onlines. She received and offer and just had to take it (ironically) to a local Toyota dealer for the final appraisal and sold it....for $9k.

We did the same with my Expedition through CarMax. I had it listed at $18k privately with no bites. Sold it to CarMax for $19,500.

I'm relieved to hear this....I'm only in a hurry to buy b/c of the warranty...figured I'd be wasting a major feature. If not, your advice sounds solid. And makes things simpler: find a good price and grab it. Lots of 'em available, w/prices rated ("good deal," "fair price," "very high," etc.)

Yeah, that sounds great. So much simpler to do just go w/CarMax or Edmunds (but not Carvana apparently- yikes.)

It's the standard advice especially from Consumer Reports et al. If it's not really a "thing," obviously it makes it more simple for me: either online, or just ask the dealer for the best deal inc. trade-in, and compare deals.

Think for a minute...this "advice" has been circling around for a decade or more. I'm sure the dealers have never considered this possibility and surely haven't thought of a way to recoup their money.

this is dumb 'logic' in 2022. Oh no, I don't want to make the dealer mad they may not give me what i want for my vehicle (while used car prices are at historically high prices and dealers are struggling to keep cars on the lot)

I can get 3+ offers on my vehicle without leaving the house. Go to the dealer and negotiate the price on the car you want to buy, lock it in, and tell them you've got a trade. They can beat the offers you already have and make a deal or you can finish with your carvana/carmax/edmunds/etc deal and come back with a check

I sold my 2019 ORP to Vroom with 19K miles for the same as I paid OTD three years prior.

Wow. But I believe it. I paid $36,500 for my Outback Onyx XT in Nov. '19 (granted, it was a great deal; other dealers wouldn't go below at least ~39K), and KBB gives the expected sale price w/19,000 mi. on it as $36/37K....$35-36 as a trade-in.

Well, that's interesting.....that does make sense: get some offers on my car, go out and get an agreed price for the runner, present the trade-in offers, give them a chance to beat it, or at least match it, etc. There's no real pressure either way for me....I can take it or leave it; same outcome, basically.