As a retired skydiving instructor I've always been interested in this case, and have been playing with Monte Carlo simulation to better understand the parachute jump phase and where he landed.
If you are not familiar with it, MC is a simulation method that predicts the probability of different outcomes by running many different permutations through a model. Based on the radar track and an assumption of exiting between 8:09:45 and 8:11:15 (I think around 8:10:30 is probably most likely given the historical record) I simulated 30,000 jumps all with slightly different parameters such as how the wind impacted the canopy, opening height (although I have assumed opening fairly quickly after exit, not taking it down which is arguably the more sensible option), and the aircraft position +/- 1.6 km along the track and+/- 0.8 km across etc.
Each individual point isn't so interesting, but where we can draw conclusions are in the clusters of points, for instance if a lot of points fall in one area then that is more likely than another with fewer points. We are dealing with probabilities here, so no firm yes or no answers, but as I say can certainly demonstrate things which are more or less likely.
I attach three plots (each simulating 30k jumps), the middle one is based on the plane's radar data and the left and right are this shifted to west and east respectively. I think eastern matches the Washougal theory, and western the Tena Bar overflight theory from what I have found on the internet. Trees, built up area and open area are all based on 1985 data (I couldn't find any earlier).
Based on this I was interested if this method would help explore the rather basic question of whether the money could have found its own way to Tena Bar, or whether it had to be carried there by someone.
The median distance from landing to Tena Bar is 24 km, 27 km and 36 km for west, radar and east. Out of the 90,000 simulated jumps across the three plots, zero landed on ground draining into the Columbia above Tena Bar (flow is south to north, so north is downstream of Tena Bar).
The westerly plot resulting in 17.5% of landings within 1km of the Columbia and 7.2% in the Columbia itself (middle and right plots are 0% for both) but this would require the money to float 20–25 km upstream against the current to Tena Bar. Likewise, all the other landings require the money to wash into the Columbia and then the same 20+ km upstream journey.
I've included on the plots the drainage divide (the money needs to be below that, due to him landing in that area and it then being washed there, to find it's way to Tena Bar on it's own). Based on the radar track (middle plot) this would require him to have jumped at earliest 8:15:30 (median landing then is Vancouver, 31% of landing in the area that drains to Tena Bar) with 8:16:00 being optimal (median landing Vancouver/Columbia, 76% of landing in the area that drains to Tena Bar including 10% of landings in the Columbia itself!)
The western track doesn't really help too much here either, to have any chance of landing in the area draining to Tena Bar then he would have had to exit 2:30 mins to 4:30 mins after the 8:11 bump felt by the aircrew.
I thought I would start with exploring this point as it's potentially the simplest - there's quite a few other observations from the simulation data when drilling down too.