In the two decades I’ve been helping people purchase and lease cars, I’ve never seen anything remotely like the insanity facing consumers these days as they try to figure out what to do with their money. And it’s no better for those of us in the car business: week-to-week we watch wholesale prices fluctuate dramatically and unpredictably, never being exactly sure what a car, truck, or SUV might be worth.

Used prices are up year-on-year (for the first time since October ‘07), according to the world’s largest auction company, Manheim. In fact, prices have gone up for the past five months strait, at roughly 5-9% per month. That means that a vehicle that we’d pay $10,000 for at the beginning of the year now brings $12-13,000 at auction. Most affected are the mainstream vehicles people really need.

The three biggest factors here are that new car sales are off roughly 40%, meaning there are that many fewer trade-ins; rental fleets returns (where most ‘program’ cars come from) are down 30%; and many folk who were buying new are now shopping used, pushing demand up on exactly those cars that are already the hardest to come by.

But not everything is being affected; many high-end and specialty rides are still soft on the market. If you’ve had a hankering for a Porsche or Bentley, now’s the time.

Another counterintuitive fluctuation is full-size SUVs, whose prices have been going up steadily this spring and early summer. In the short run this makes sense, as gas is cheap. But longer term, once demand on finite oil supplies picks up, those pump prices will almost certainly rise, sinking the value of these behemoths beneath a flood of fuel bills.

And it’s about to get even more cookie; with Chrysler having killed 789 dealers, and Government Motors (GM) planning to get rid of somewhere around 1100 over the next year, not only will there be a lot of unsold late-model new cars, trucks, and SUVs coming into the market, affecting values on both new and used late models, but about half those who’re loosing their franchises plan to enter the used car selling fray, resulting in more wholesale buyers for fewer vehicles.

So: how do you make the most of this? After consulting my (cracked) crystal ball one more time, here is my advice:

1. If you have a decent (and market-desirable) used car, it might just be worth as much as a trade-in as if you sold it yourself. Here’s why: in many states, like Colorado, you only pay sales tax on the difference between your trade-in’s value and what the new(er) vehicle costs; if you lived in Denver, this equates to about $760 in tax savings on a $10,000 trade. Combined with the higher values dealers are giving, this could save the hassle of selling it yourself.

2. If you’re after a Chrysler, Dodge, or Jeep, the time is now! Chrysler has given notice to 789 of their franchises that they wont be allowed to sell the company’s new products. They have about 26,000 remaining ‘old stockers’ to be redistributed to surviving dealers—who may not want any more leftovers to bloat their inventories–which will only make the deals better on these vehicles—and, if they’re planning to become a used car store, they may want your trade-in for their inventory.

3. General Motors will be closing about 1000 dealers over the next 12-18 months, so there’ll be deals to be had at their franchises as well (though the timeline for their wind-down is longer).

4. Cash for Guzzlers: winding its way through congress is legislation that could pay you $3500-4500 for your older car or truck if you trade it on something more frugal. They’ve now separated this bill from contentious (and slow moving) energy legislation, intending to fast-track it into the limelight. When (if) it passes, it is only supposed to apply to the first million new car sales, so watch this space! The details are here, and here (for those of you who can read congrese).

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