1. the first time you install CyanogenMod its very slow to start up. Just be patient it takes a while to load that first time. After that it boots instantly, much faster than WebOS.
2. Get ES File Explorer - it's awesome especially if you have a NAS. I can access it from anywhere via FTP. Live streaming of music and movies from anywhere.
3. MX Video Player is the most compatible with the most formats.
4. ES Task Manager is another great app to have.
If you download anything from the market that doesn't run (games usually) you can get them to run just by changing the name of the system in a configuration file. I got Shine Runner working by changing it from 'HP Touchpad' to 'HTC [something]'. Doesn't effect anything else really. Some apps just check the system name and won't run if its not an 'approved' system. But the touchpad hardware can handle just about anything even if the aspect ratio gets a little skewed. Google the CyanogenMod forums to get more info about stuff like that. You can get Skype video working too, it won't work from the Market install, but there's instructions on the forums on how to get it working.
Also updating is very easy. You can update from the boot menu, but even if you ever had to reinstall from scratch, after you have installed once you won't be scared to. It's an easy process and the first time was just intimidating because it was unknown for me.