My brother never listens to my advice, a few years ago he started his SBC after a winter layup and spun a bearing
FYI: When I start my engines after a long layup (> 2 months) I like to prime the oil system and clean the carb (on carb engines)
I spray a judisious amount of carb cleaner in the Holly sight holes. Let cleaner soak a few hours.
When ready to start the engine, I disable the ignition (ground coil wire) and crank the engine over until it builds oil pressue (check oil pressure at the gauge). I do not crank over 20 seconds at a time so the started does not overheat. Let engine sit for five minutes and repeat.
Your bearings will thank you!