There isn't any "starting out easy". The guy has only four completed albums and each of them play like a Greatest Hits record. Start out with whichever suits you best:
Electric Ladyland - psychedelic noodling
Axis: Bold as Love - Pop Rock
Are You Experienced - pop rock/psychedelia blend
Band of Gypsys - Funk
ignore "First Rays of the New Rising Sun" until you're familiar with everything else.