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This is a great post. I'm in the same boat and looking for a similar vehilce. While I do agree that the RAv4/CRV and Outback are all great choices, they don't meet the less than $5,000 that the OP listed as a maximum price range.

Wrong.

I purchased my 99 outback with 115k in October of last year for $4700.
It's in great shape and runs like a top. Getting an average of 26mpg is a nice plus too.
Gas mileage was a big reason I sold my 02 tahoe and bought this. 12mpg in a 7 passenger tahoe was too much when it was just me and my dog %95 of the time.

Rav4 and CRV's can be had in that price range also, but I've had experience with both and i'm not a huge fan.
If it came between those two, i'd choose a 1st gen crv. The b20 engine is reliable and easy to work on.
 
You can easily get 1st and 2nd gen outbacks for under his 5k price range :). i picked my 01 up for 2899. I have seen tons of low miles first and 2nd gens for 2-5k.
 
Thanks for your continued input!

Does anyone have any tips on how to avoid dealers posing as private sellers on Craigslist? I have come across a couple and would prefer to deal with private parties only.
 
Another vote for Subaru. The '80s GL wagons are cheap (bought and drove home my last one for $350) and extremely easy to keep on the road, though they require some regular maintenance. The Legacy series is more reliable and I vastly prefer the pre-97 ones, due to the non-interference EJ22 motor design. Outbacks are great, but I'm not a fan of the phase 2 motor design (interference). However, using early dual-port EJ22 heads on a later EJ25 to make a frankenmotor rocks!
 
You can find good examples of a number of different vehicles. But in that price range you obviously have to compromise. Anything you buy for $5k will need some TLC in one area or another. The trick is to choose your poison wisely.
If you are a good wrench, find something that needs fixing in a component you are comfortable working on.
About a year and a half ago I bought a 2001 Nissan Xterra with 120k miles on it. It needed had a coolant leak in the manifold and it was about an $800 job but other than that and putting good tires on it, it has been a super car. Hauling 5 people and gear all over.
I have had it hunting, pulling a utility trailer, handy roof rack. Plenty of rear space behind the hatch for an average size pooch. Because the Xterra has independent front suspension it is a fairly comfy road car. It's a bit of a compromise if you want to do some heavy off roading but I find it's a fair trade off.
I would also look at Ford Escape, Jeep Liberty, Honda CRV and you will even find some Nissan Pathfinders in your price range. You will be hard pressed to find a Rav 4 in your price range.
 
And like others here I would also suggest looking at Subarus. We just bought our first one. It's a 2005 Legacy sedan with 87k miles. Very nice car and runs great.
One thing that seemed interesting to me while I was shopping for it though. There are a lot of Subarus on craigslist with branded titles. Not sure why that is.
Just be sure to ask about the title right away to save yourself some time. Unless you don't mind having a car with a salvaged title. Some folks are ok with that.
 
When you narrow your choice down, look for a forum. Ask those folks how the one you're looking at goes - giving them you use of course. I'm a long time Mitsubishi aficionado (http://www.4x4wire.com/forums). Many other makes have their own sections at that site. I haven't read the others, but the Montero/Raider/Pajero etc. guys are genuine experts.
 
I second the Volvo recommendation. The modular engine they are using has been around almost 20 years at this point, and is mechanically solid. I have read a number of technical publications, and it seems that their goal is 20 years and 200k miles before major work being required on the engine (granted they do use timing belts...). My old 850 at 180k is in way better shape than many of the Japanese/US cars I have had with fewer miles, and the family fits in it great. The XC70 is newer than the V70 and V70 XC, which are newer than the 850 (the original V70 and 850 are the same platform though).
 
I'd get a small truck, preferably an extended cab, and put a canopy on it. A child can sit in the extended cab (even in a car seat), you could p[ut the dog back behind the seat and have three people on a bench seat, or dog could go in the bed under a cnaopy- which also gives you room for any gear you need, and even a somewhat-secure sleeping space (secure against small animals, but not a bear or a human.)

I find Ford Rangers to be a good value. They don't retain a lot of resale price, but they run forever with decent maintenance. They get good gas mileage in the 4cyl version, and you can get 4WD. One of the more basic models simply has less stuff to go wrong with it.

The ability do transport cargo is the best reason to get a pickup instead of a wagon or SUV. Even with fold-down or removable seats, you simply can't carry as much stuff as a pickup will. You can always take the canopy off and pile stuff high, or drop the tail gate and let it hang over. If you can't get an extended cab, in an emergency situation, there's no reason people can't ride in the back, especially with a canopy over them.
 
Just to avoid any confusion, I like the Ranger, but there are no child seats that will work in a fold down side seat. If you want a truck you would need a real back seat.
 
My Wife currently drives our Hyundai Santa Fe, and it is a great SUV. It gets in the mid 20s for mileage, and you can even find models with 3 rows of seating. The early 2000's models should fit into the OP price range, as well as not being 'TOO BIG'. They are comfortable, and realiable with parts prices being reasonable as well.

I was surprised to not see any mention of Hyundai until now. We love ours, and our next vehicle will be a KIA Soul (Made by Hyundai), which will be a commuter and car my kids will learn to drive in.

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Capitalism is BO$$!!!
 
Another vote for the Subaru. Look at the Forester. Meets all your requirements. People hauler, pet hauler and anything you want to throw in the back hauler. Handles great, solid Subaru AWD and goes anywhere, plus good mileage.
 
Really like our Outback! Roomy, comfortable, reliable with pretty good fuel economy. That said, I also have a Dodge Dakota (PU version of the Durango) 4 door, short bed. Even more reliable, comfy but will go ANYWHERE! We just did a 1,700mi trip to Elko NV. including 82 mph (75mph speedlimits), mountains and 4wd varmint hunting. 19mpg. Oh, 4.7L-V8. I love my truck! Oh again, Grandson and 135lb dog in back seat.
 
Just keep in mind that Rav4s, CRVs and Subarus, though they can be had with 4WD, are not serious off-road vehicles. They have poor ground clearance, unibody construction and lots of delicate suspension parts hanging down where a rock will crush them. They are fine for dirt roads and such, but that is about all. SUVs like the Pathfinder, 4Runner, Blazers, Cherokees and the like have tough suspension, full ladder frames and the ground clearance to actually go off the road.
 
I make my living repairing cars. This is my personal experience with the following vehicles:
-Accord wagon: Reasonable maintenance will get you 300K miles. Kind of tough to find now.
-Camry wagon: ^^same^^
-Legacy wagon: Again, good for 300K. AWD and will go anywhere you need to go. Head gaskets are an issue generally between 1996-2006 models. I wouldn't pay extra for an Outback as you really gain no extra capability. The Forester is a tiny bit roomier. All are mechanically very similar.
-Volvo wagons: The fwd 850/V70s are great cars and very reliable. Awd is a nice upgrade but I believe it's only available with a turbo. The hard parts are really no more expensive than the others. They can have weird electrical quirks though. For example, I've seen a bad ABS module cause O2 sensor codes. The older 240/740 rwd cars are tanks an will go forever. Expect to always have some small problem.
-4Runners are always great. They have a well documented head gasket issue in the V6. The 4cyl version is tough to find but would be my preference unless towing is necessary.
-Cherokee/Grand Cherokee: The I6 version is great. They aren't very refined but are extremely rugged and reliable. Gas mileage isn't great.
-Trailblazer/Envoy: Seem to be proving themselves as reliable but may still be out of the price range. I've seen several closing in on 200K with a reliable history.

I would avoid baby Blazers and Explorers. They're cheap to get into but expensive in the long run. Durangos are OK but are not known for their refinement or efficiency. The Rav4 and CRV are OK but I don't feel you get much for the money. Mitsubishi and Isuzu parts are expensive. I haven't seen many Kias/Hyundais past 100K that didn't have nickle and dime type issues.

You sure you don't just need a minivan?
 

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