Replacing a Star

My wife had a 97 4Runner and my friend has a 99 4Runner with 210k miles he's selling for a newer Tundra. It is really amazing how far they can go.

The Toyota RAV4 is probably a good choice. It'll have the reliability you are used to with your 4Runner (maybe a little less durable than your 4Runner). Easy to see out of, has 4 wheel drive, cargo space, smaller than a 4Runner. It is boring to drive however. Even if you get the cheapest trim level, the LE, you still get all the active safety features standard. Has a 3,500 lbs tow rating with the Adventure AWD trim. The Hybrid is rated to tow 1750 lbs. You may want to buy the Hybrid RAV4 to sacrifice a good AWD system and tow rating for higher MPGs.

The Mazda CX-5 would be more fun to drive, but won't be as easy to see out of and reliability won't match Toyota. It is still very reliable. Has a little less cargo space than the RAV4, but not by much. It feels like an entry-level luxury SUV with the beautifu exterior and high-quality interior. Has a 2,000 lbs tow rating.

A 2018 Subaru Outback 3.6L might be the best option. Easy to see out of, more powerful engine, cargo space, active safety features are available, comfortable and quiet, lots of cargo space. Has a 3,000 lbs tow rating. The 4wd system is the best in this one. I would worry about reliability more than the Mazda or Toyota. Oil consumption has been a problem with Subarus, but not really with the 3.6 engine. Gas mileage would also be lower in this than the Mazda or Toyota.

I'd skip the RAV4 from 2013 on up as the AWD wont send 50% torque to the rear wheels even with it locked up. It only sends 25% to a single wheel when locked and it is not enough to power the car. The RAV4 couldn't even make up the hill backwards as seen in the videos below. I'd also skip on the hybrid version as the only way to back up is on battery which is iffy with a trailer. While most of these 4-cylinder compact SUVs mentioned above will net you 4-7 mpg better than you have now, none of them will match the 5,000 lbs towing capacity of the 4runner. I'd definitely look at v6 or turbo-4 for any towing especially when it comes to elevation.
A Terrain or Equinox 3 6l is rated to tow 3,500 lbs and has 1/3rd more power than the 4-cylinder subcompact suvs and your 4runner. The AWD shuts the rear wheels at highway speeds when it is not needed. A 2017 Acadia or Cadillac XT5 with have a 2wd mode on their AWD systems and the 3.6l has AFM(active fuel management) that shuts down cylinders similar to deceleration fuel cutoff(DFCO) that let's thr engine freewheel while coasting owners have reported getting close to 30 mpg with the 3.6l AFM and either can be found online right at $40K. A 2000 Tahoe would have cost slightly less than you paid back then for your 4runner, but offered a 4.8l or 5.7 v8 and be worth similar today. Otherwise I'd keep the 4runner and just budget maintenance and repairs along with a AAA membership with 100 mile towing as a new one really hasn't changed that much. Depending on condition your 4runner may be worth $3,000-6,000 dollars today. AWD-I TEST: 2017 Toyota Rav4 Hybrid | Diagonal Snow Ice Test | Complete Review: Part 6/8

AWD-I TEST: 2017 Toyota Rav4 Hybrid | Diagonal Snow Ice Test | Complete Review: Part 6/8

If you want to buy a compact SUV, well get ready because there is a lot of choices! But if you want to save some fuel and you are looking for a Hybrid versio... 2016 Toyota Rav4 AWD - Review & Offroad Test Drive

2016 Toyota Rav4 AWD - Review & Offroad Test Drive

2016 Toyota Rav4 AWD Review - Offroad Testing. The 2016 Toyota Rav4 features a 2.5L engine, 6 speed automatic, and available front wheel drive or all wheel d...

Your 4Runner will probably sell for around $4-5k if it is an SR5 or higher if it's a Limited. Even more if you have it modified to off-road.