The latest S-series is a great-sounding device, lightweight and is relatively affordable. Your 'dropping' habit however might be the proverbial deal "breaker", though...the S-series is a plastic-bodied unit and as such is probably going to crack at some point. Sony does make a silicone protector for it so if you do go this route it'll probably be mandatory for aiding in the survival of the device.

Video loading isn't fun with ANY Sony Walkman, but it's doable. Once on they look pretty good. Audiobooks isn't really in a Walkman's bag of tricks. You can drag 'n' drop to a Walkman, or you can use a good 3rd-party manager like MediaMonkey in lieu of Sony's own software for audio, but for vids it's best to use the Sony app (which isn't saying much). Extremely good battery life (according to Sony, up to 42 hrs for audio only), easy to use UI though not as good (comprehensive) as earlier Walkmans, FM radio, fully tactile mechanical controls, built-in speakers, 16GB (S545 model), available in black and red for the 16GB unit. Even has voice recording, but definitely NOT a key selling point.

Some downsides are that it's a bit sluggish compared to earlier Walkmans, and there's fewer DSP tweaks built into the player than Sony's previous devices. But at $109 (current price on Amazon), it's hard to go wrong...well, except for that dropping habit of yours.