I had a 97 ES300 with +280k miles up till March 2014 in this harsh Canadian road (with salt).
When properly maintained (i.e. oil change, fluid change, etc), there are no major issues.

At +280k miles, it had a major oil leak. I suspect it was the rear main seal but I got rid of it.....

 

I'm with you on the around $3k price, $3800 is too high imo. The 97's have the more robust transmission and the non VVTI engines. I don't remember if these are non interference or interference engines. All years of the 3rd gen are great, you won't regret buying one.

 

My '05 ES does great in the winter, because it hasn't been out of the garage since Thanksgiving. It sucks in the snow, but mostly because it doesn't have proper snow tires. That's what I have a 4WD pickup truck for.

If in your shoes, I would go with an RX. Our Highlander is awesome in the snow, although we did get ours stuck in the driveway the other day, when we tried to drive it through the 5' high pile at the end from the plow. I tried to tell her it wouldn't make it...

And I have enough experience with Subarus that I wouldn't take one of those things at gunpoint. Once you drive a Lexus (or any other "luxury" class car) there is no way you could live with one.

 

I looked at emdunds.com (what I use when buying used) and that mileage, excellent/outstanding condition and most common features says $2,600 trading in, $3200 private party, $4250 dealer retail in Lewiston, ME (zip code I chose out of a hat).

You can go hear and play with variables to see:

http://www.edmunds.com/lexus/es-300/...e-results.html

So it sounds like a deal could be struck and it could be a great car. The cw is that non-VVT-i motors are non-interference and VVT-i ones are, which stands to reason given how much the VVT gear alters intake timing at various rpms. Thus, since that's non VVT-i, you can worry less if timing belt change is not documented. A broken one, pulley, or tensioner (they can all fail, not just the belt) would be a tow home and not a lunched engine. If the t-belt change is not documented, then that's a serious negotiating point.

If I could find a REALLY clean 97 with 120k miles and documente 3k oil changes, I'd snap it up even without the newer design, VVT-i (it is a nice thing) or the 5 speed at.

 

Comparing the ES300 (with the 3.0L 1MZ-FE engine) vs the ES330 (with the 3.3L 3MZ-FE engine):

I have a Toyota Solara with the same 3.0L engine as the ES300, as well as an ES330 with the 3.3L.

I can tell you if you value refinement and responsiveness, the cable driven older 3.0L engine is much more refined, smoother and quieter than the 3.3L engine. The throttle response is instant and the car really flies, where as with the ES330, the throttle lags and it feels like you have to punch it hard for it to move.
The transmission in the ES330 is economy tuned to keep the RPM's low, which make it slower around town as you've got 3 gear changes before getting to a measly 30 MPH.

Nevertheless as others have mentioned, the newer 4th generation ES has a much better interior, than even new cars today.

 

Any Updates? Which did you buy?

Here's my 2 cents.

My 98 ES300 ran great at 342K miles until it was rear ended and totalled by the insurance company. I was bummed cause I wanted to see how long it will last with just routine maintenance (was hoping for 500K miles). These cars are solid as long as you get one that has not been abused.

There are a lot of used Lexus under $10,000, you just have to find the right one. It will take some time. There are a lot 4th Gen ES in this price range however I just like the more responsive throttle of the 3rd Gen and I prefer it's older styling. Both cars have their Pros and cons but you can't really go wrong with any of them, it's just styling and driving response that you have to choose.

 

As having owned a 2001 and now a 2004, I'll be honest I liked the 2001 more in terms of driving and looks...but the features on the 2004 more than make up for it, and it's a lot comfortable. As for being bad in snow, the ES is far from it, with snow tires it's actually quite good. I also have a 2002 GS300, and with snow tires it can be a pain, but not terrible. For winter driving, it really comes down to tires. I've also been driving a 1999 4Runner and while it's better from a stop than the ESs or the GS, becauE it only has all seasons, it doesn't brake or turn nearly as well as ether the ES330 on dunlop snows or GS300 on michelin snows.