Thanks for the response!!
Is there a reason for getting much newer? besides it being newer!!..lol
What year(s) do you recommend? or does it really matter!!!
I'm from Fairfax City area. Welcome to the forums!
First off, you're in the right place. The fact you already decided on going with a Toyota implies you're willing to spend some $ for a quality vehicle that will last forever with proper maintenance. You're a smart man and your son is lucky to have a dad with common sense.
Now onto your question...it being your son's first vehicle, I would strongly recommend buying a 3rd gen as a starter vehicle. If it's your son's first vehicle, I am assuming he is still in high school and does not have a bunch of driving experience which is totally cool. Unless your income allows you to make expensive purchases at a moment's notice in event of an accident, I would go with a cheap well-maintained 3rd gen for your son so he can be more comfortable with it.
My first vehicle was a 3rd gen '99 and I loved it. Insurance rates were cheap at the time. Previous owner had an insane maintenance history so I was fortunate to have found a vehicle that was cared for by the previous owner. It got me through hard times, bailed me out of nasty weather situations and it saved me from being injured when I got into an accident driving 35mph.
As you can see in the picture above, this was a well-built vehicle. I actually wanted another 3rd gen with the same year but unfortunately no 3rd gen matching my specs. were available on the market...so I ended up getting an '04 the next day.
3rd gen is kind of smaller compared to 4th gen but it's good enough for teenagers IMO. Others may disagree with me on this but 4th gen 4R is a 'luxury' vehicle compared to other older SUVs on the road today and more expensive in terms of sale price and insurance rates. Plus 4Runners in general have a high resale value due to vehicle reliability
If you both test-drive a 3rd gen or 4th gen and interested in buying it, make sure you take it to a Toyota dealership to have a full pre-purchase inspection so you can see what parts need to be replaced and factor these into the final price when negotiating.
Don't even think about buying a 30k+ 5th gen for your son unless it's for you...I'm not even happy with Toyota wanting to add more electronics on 5th gen 4Runners. It's ridiculous but that's just me.
Here's a little more info. on 4th gen 4Runners in terms of year
http://www.toyota120.com/html/4runner.html