LBM,
I used to live in So Cal and boated in the Pacific Northwest.
After a summer of boating I had to trailer 1500 or so miles. I wanted the aft end of the trailer light, so I pumped the remaining gas into my towing vehicle (1 ton van) and into 5's to be poured into the van. I also removed the SS prop.
The boat was stored in relatively warm conditions, so condensation was not much of a problem. I also did not want to invest in 50 gals of gas and stabilizer and let it sit 8 or 9 months, evaporating the lighter hydrocarbons leaving old gas.
From what I hear, the new E-10 gas doesn't store well, and some 'experts' recommend pumping the tanks for winter.
I have since sold the C-Dory and in my trawler I now have to deal with stablising up to 360 gallons of diesel for winter storage. I fill my tanks when I guess the price of fuel is at its lowest price before the spring price run up and add stabilizer. I filled my tanks in Jan and now have enough fuel for a 1,000 mile summer.