postscriptum
Dont' worry about the oil filter. Just go to the toyota dealer and buy a new one for like $4 and change. OEM Toyota filters are better than anything else you'll buy aftermarket. (Toyota shares many filters between engines) You can choose between a small one and a larger one. The engine doesn't care which one you use.
Buy the small one, it costs $1.50 less.

It's not like an engine is going to clog the filter if it's not about to die anyways.
The 1mz-fe v6 should be able to get you atleast 28mpg on the highway.
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I want to know about the engine sludge problem I keep hearing about. How real is this? What about oil leaks?
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Oil *sludging* is caused by simply not changing it at anything near normal mileage. The Lexus brand issued a statement a few years back that engine sludge was only common place for people that left the original OEM oil in the car for over three years without changing it. (that's goes for the 3vz-fe, and the first two iterations of the 1mz-fe)
All Toyota v6 engines from '89 on have full lifetime warrenties on sludge damage so long as you can prove you have changed the oil once in the past year, or 10,000 miles. Sludge is not a common problem for anyone that does any maintanance.
Oil leaks happen eventually with any car. The rear main seal, rear head gasket and rear valve cover are prone to leaking after a relatively short 60,000 mile life. Most of the time you get a normal full life out of them.
1)The valve cover gasket has to deal with the tilted back angle that the rear bank has. (oil has the habit of *pooling* there and not flowing out quickly)
2)The head gaskets can leak. This is a problem most manuf. faced after the federal government banned the use of asbestos as gasket material.
3)The rear main seal is a pain in the ass to change, but most of those that will fail, already have been replaced.
That's the only problems that ever tend to crop up with oil. Don't let me sound like it's often, but when it happens there are your #3 most common big areas.
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what specific items should I pay attention to, and what maintenance records should I want to see?Timing belts done? Is OBDII easy to read?
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The only records you need to see when buying any Toyota engine are records of oil changes, and transmission fluid changes are a bonus as well.
You should check the coloration of the transmission fluid. If possible drain some fluid and check for metal flakes. (same as with any car)
To check for oil leaks, take a flashlight and look at back the rear bank on the V6. No oil streaming down the back = good seals. No problems.
The timing belt should last a really long time, but Toyota recommends they be changed every 60,000 miles. My ES was done at a Lexus dealer (they have a computer database woot) at 60,000 miles and it looks almost brand new @ 105,000 miles. Their life is commonly stretched to over 110,000 miles<form own opinions here>, and since toyota makes not interfferance engines. if the timing belt snaps it doesn't matter what position the valves are in. They will not be damaged.
OBDII is very easy to read. They are many aftermarket OBDII systems that are able to read the ECU, and do neat things with the information. (Like accurate HP and TQ to the wheels)
It's an older Toyota, all replacement parts can be had for cheap as long as you don't buy expencive ones from the dealer.
I, personally, would buy the Toyota. Parts are 300X more avalible if something happens and as such they're easier to repair than a subaru. Any mechanic can do the majority of work on them without being confused also. Like you said they don't look silly.