me, I'd split my electrical load into: critical; more-or-less essential; and, other. Two new panels, two auto-transfer switches. Feed the critical panel through one AT sw from the more-or-less panel. Feed the more-or-less through the other AT sw from your current mains panel. Two gensets, NG and Diesel, one to each AT sw. Me, I would size and fuel the (smaller) critical one from NG and the (higher-amp) more-or-less from diesel ...but you could do the reverse ...choose your scenario. [if you followed the above description, note that the smaller genset automatically cuts out when the larger is running].
Why would winter starting be any harder for the diesel genset than for any other diesel motor you have? Same winterized fuel, block heater and extra parallel deep discharge batteries optional ...[and, note that except in your catastrophic earthquake scenario the NG genset is running while you fiddle with the diesel if, indeed, you have to.]
I would not think that 800 amp service is required in an "emergency" ...and, if I had natural gas and adored AC, I would have installed gas-powered AC units, which have higher installation costs but lower operating costs.
...it's fun to plan survival scenarios with OPM (other people's money)