Kbrewer, After looking back at this thread again this morning and seeing how the conversation has turned toward Cadillac timing sets, it becomes glaring obvious that I neglected to point out that the timing set you want to use is a Cloyes 91-139 (better confirm that number, as I have CRS). This gear set is not the 'double roller' that the advertisements claim, but it does include a healthy chain and two steel gears. The crank gear has three keyways. The one, will allow you to advance the timing a little, which will help your cause with a direct drive.
I didn't, but maybe should have elaborated on that point previously. The standard, OEM gear set had some kind of glorified plastic teeth that seemed to suit the purpose for the time being. However as the decades passed those guys got beyond brittle and liked to break off. This may well be your problem, in fact, if the rockers are all where they belong (ie. intact), then I would bet this is your issue. A word of caution in that regard... Be sure you drop the pan and thoroughly clean everything, to include the oil pick-up tube. You will likely find that shit everywhere, because the the last guy probably didn't do that and there remnants of more than just the current incident. The way that pick-up is constructed it will suck up and hold all of those little broken teeth pieces. Removing it and running pressurized air or better yet, water through it backwards, is generally the most thorough and time effective means of doing that. On that note, be aware that front gasket set will include two o-rings for the reinstall of that pick-up tube (one is for the 425). Confirm you use the right one, when you reassemble it!
As far as the Double Wide Keyway goes . . . What OEG and John have reported is much more common than most people reading this realize.
At a glance, this all reads like the crank gears are inferior or somehow defective. That is not the case. This is not something you see happen in an old land barge. This occurrence is quite specific to an air boat application (dd especially), and is in fact, quite common where the hours have been amassed like the boat owner would hope for. Consider if you will, that with the mass of the prop bolted directly to the crankshaft, EVERY TIME you let off the throttle . . . you not only have the mass of the prop and the valve train acting as a brake, but you also have centrifugal force of that mass, plus the wind resistance the prop USED to be pushing. While the crank and all its weight and mass are turning Clockwise, when you let off the gas, you have everything just listed attempting to turn Counter-Clockwise! Something has to give (or wear), and that something is the crank gear keyway. I had some pictures of this hacing happened that were quite impressive, but sadly, that computer is no longer with us.
One last thing . . . Be Aware before the fact, that the instructions with that timing set are less clear then black mud. Search here first, or at least be aware that those gear set instructions are left-handed, backwards, inside out, upside down, etc. IIRC, If you install the timing marks in standard fashion with them both being UP, you need to install the chain with #4 at TDC, NOT #1. Then turn the assembly to #1 TDC to stab the distributor. Again, this is from memory, so double check it when you get that far. In any case, don't be bashful about asking questions. These old Caddies have their idiosyncrasies, but there a few of us left willing to help when we can.
Let us know what you find when you tear into into it. A few of us are more than passively curious.