In answer to the first question, you're welcome to visit my website http://tariffhound.co.uk which provides friendly help and advice to families about their mobile devices.
To solve your problem, we need to figure out where to keep yours and DS' iTunes libraries on your laptop. The choices are: 1. Keep separate iTunes libraries on the laptop
The key advantage here is that you will have separate iTunes libraries so you don't need to wade through each other's music when you want to choose to put something on your iPod or iPad.
The disadvantage is that to do this, you'll need to set up different log-ons for the laptop. You don't mention what operating system (i.e. version of Windows) your laptop runs, but the recent ones allow you to set up different logins for different members of the family. Hence when you login as yourself, you will get iTunes with your information, when DS logs in as himself, he sees his iTunes library.
To get this outcome, you need to be comfortable setting up and using the different laptop logins.
The alternative is:
2. Keep a combined iTunes library This is probably how you are set up now, so that you share the same administrator account when you log into your laptop, and you both see that same iTunes library.
The advantage of this approach is that you don't need to do any tweaking to your laptop. However, all your songs and albums are going to be jumbled together in the one iTunes library.
However you might feel that although this is not ideal, is may not be that painful to wade through each other's content when you want to put new stuff on your iPod or iPad. I guess it depends on how often you do this task.
Finally, why did you lose your songs when you synced? I think you may have had songs on your iPod that weren't in your laptop's iTunes library.
Your iPod is a monogamous thing - it can only be "married" to one computer's iTunes library at any one time. If you have songs on an iPod from one computer's iTunes library, then try and sync your iPod to a new laptop who's iTunes library doesn't contain all the songs on your iPod, the songs on your iPod but not in iTunes get wiped. It's a legal thing to try and top people borrowing a mate's iPod and grabbing all their music and transferring it to their iPod.
Let me know how you get on and if you need any follow up advice.
Are there any online help sites that are simple to understand? Have a 3rd gen iPod, an old laptop with iTunes, and an iPad. DS has iPad and his own shuffle iPod. I've just synced iPod to laptop and lost a bunch of songs. I want to separate his stuff and mine (don't care much for Scrillex!). Just can't get my head round it (never have!) Any tips/advice? Thx