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My first oil change will be coming up on my '09 HL which I plan on keeping for a while. Should I make the switch to synthetic now? How long between oil changes if I make that switch and what differences while it make in the short and long term? (other than costing a lot more per oil change). Thanks.
 

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You could switch to a synthetic any time you want.
Differences depend on you, your driving style, the oil change interval you choose, the oil brand/weight.......
My personal experience is a longer lasting engine with less performance degradation over time.
Depending on the weather, you might see better MPG, as synthetic usually is easier to pump/flow when cold.

Per your owners manual, you are required to make 5k oil change intervals regardless of the oil you use.

If you are a rebel, you can analyze your oil and adjust accordingly per your driving style.
 

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I would also recommend a switch to a full synthetic too if you keep you cars/truck for a long time. Many cars now come stock from the factory with synthetic. But if not, I put it in at the first oil change. Use a good quality filter too.
 

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Switch. You won't regret it. If you change your own oil it shouldn't cost much more than $35 each time even with the filter. I run synthetic in everthing I own. My Highlander will not be any different. I've only got 600 miles on it so far so my first change is probably a few weeks away.
 
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