It is possible to get your sneaking to 5 (with the help of gear) by level 4, assuming you took sneak at character creation.
I'm back playing the game from a long absence and opted to go with a stealthy archer with Guerilla and Bully. Given the fact that an archer attacks from a distance, dropping in and out of sneak is fairly easily obtained.
As a rogue I would think that this would be much more difficult (i.e. attacking from sneak and going back into steath mode) given your close proximity to your target?
