"Will a 39 caddy c8 bolt up to a modern auto transmission?" Hard to get those C8s bolted up to anything!
On the FlatCad, we did a lot of work with our custom crankshaft to mimic a FE Ford rear crank flange - and then worked with Wilcap (Pat McGuire) to setup an adapter (all working from the same dimensions). I would call Wilcap - they are the best folks to deal with the oddball stuff and have made a lot of adapters for the most goofy of shit (which a Flathead Cadillac is the founding father!). My guess is that it is definitely possible - with a custom trans adapter, custom flywheel and the associated $$$ - anything can be made to work! (Plus - Pat has the geometry/CAD designs that you need to do the work!).
There is a thread on here somewhere about fabracating a bellhousing for a flat cad. something like "caveman bellhousing" do a search
http://www.transmissionadapters.com/ Bentsen's do a lot of odd ball stuff, a reputable company and great to work with, recommended!!