Love those old caddys.
A few years ago I considered swapping a 15 year old BMW with big issues for both a '65 CDV and a '68 CDV, package deal. Nice cars but had some rust issues. Supposedly, the '65 had such low miles, it still had the original bias ply tires. It also had a rusty frame
These days, though I think maybe I should have made the swap.
3 things come to mind for your starting issues.
1. My first guess is the starter motors may be getting too hot due to their close proximity to the exhaust manifold and pipe. One can get starter motor heat shields for this.... many Chevys had such shields as standard equipment. Such shields are available aftermakret, or one can wrap the pipe and manifold in "header wrap".
Lots of high compression, big engines have this problem, especially, GM products, in my experience.
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2. The starter motor may simply be worn-out. Sometimes, worn armature bushings will allow the armature to drag along the inside of the starter motor housing. A rebuild kit is usually pretty easy to install for these starters.
3. The mechanical advance weights in the distributor may be rusty and/or sticky, or the weight springs are weak or broken. When this happens, the weights do not retract when the engine stops, and allow the ignition to be over-advanced, which causes slow cranking. One can inspect the weights and springs. New springs are easy to install and the underside of the weights can be sanded smooth with #220 sandpaper. Don't oil the weights.... that will attract dirt and then they will stick like crazy.