Originally Posted by MParr
#1. VW Tiguan
#2 Hyundai Santa Fe
These would be on my recommendation list, too, if looking new. Can get either for your price. Both are, IMO, still mid sized although with how crossovers are categorized now they are on the small side of mid sized.
Speaking of price, TrueCar is a scam, for new especially. Go onto forums for whatever models you are considering. There should be a thread talking about prices paid, how to negotiate, etc. I saved about $2500 by doing that a few weeks ago on a Highlander.
Speaking of which, you could get a 2019 Highlander right now for a great deal. With a little leg work 13 to 16 percent off MSRP before the $3000 rebate is common because the 2020 redesign is hitting lots in Dec. There is an extra $500 rebate right now for being a USA Triathalon member ($50 to join).
4 cyl 2WD base can be had between $25k-$26k plus TTL. Add $2500 to $3000 for V6 and AWD. Just V6 and no AWD adds about $2000 to MSRP, maybe $1700 after discounts.
https://www.toyotanation.com/threads/prices-paid-and-possible-deals-discussion.732258/page-138
I think you need to look at current models... base models come with a lot of features now days. Put $900 to $1200 into a base Highlander to add LED headlights and fogs (comes standard with many safety features and LED tail lights), remote start, and a better stereo head unit and you would have a great car made to last with a lot more room than you are used to, and can even tow 5000 lbs with the V6 (factory hitch and wiring is about $500 and not a hard install).
You are looking to keep a while and new will typically give you a longer life than used, cheaper financing, better warranty, etc. (Highlander made in eastern Indiana). And after owning a 2013 Elantra previously I won't go back to the Korean brands.