I will have a $7,000-10,000 budget. I've worked on most of my cars in the past and found it enjoyable. However, my latest cars aren't so easy and even though I have less time when repairs are needed, I hate paying a mechanic for something that should be easy fix but isn't. With this in mind, should I go for a 2009 - 2012 Highlander or try and find an early model even though it will have a lot more miles. With Toyotas reliability, I'm not as afraid of buying something with over 200,000 miles as I would be with other models, and from what I gather, parts should be fairly cheap and easy enough for me to bring it up to newer standards. If it makes any difference, I will be towing under 1500lbs occasionally, and due to a planned moved would like to have 4 wheel drive due to where I will be moving to. thanks
Avoid the early ones (2001-2005). They have oil sludge issues. You could go for the second generation of the highlander- have a mechanic look it over before buying and take a test drive to see if you like the car.
http://www.toyotaproblems.com/oil-sludge/
https://www.carcomplaints.com/Toyota/Highlander/