Servicing is the same as for any bike except for the Headshok, about all you can do to that since you don't have the necessary tools, is lube the needle bearings under rubber boot which would be a good idea as this is something that gets neglected. Give it a good clean before removing cable ties as you don't want any dirt getting in. A full stripdown/rebuild if dirt gets in is only option, mega commitment if you've got tools, expensive if not. Slide the boot down and lube the exposed sliders/bearings, cycle fork up and down to move grease further up into bearings. Don't use oil, it just drains away, Cannondale specify a special grease but you're not likely to find any. I just used a decent bike grease, not too thick nor too runny.
The rubber boot does look compressed a bit, think the fork has a coil spring with an elastomer inside it, fairly sure it doesn't have anything more sophisticated. The spring should be OK but the elastomers do tend to die, they are tapered like the spring so replacement will need to be same shape as it fits inside spring. They are like rocking horse shit. You could try shaping an elastomer from something like an old Rockshok fork. Think the travel on these Headshoks is 60mm so not much, need the elastomer/spring to be OK or you'd be as well riding a rigid fork.
I took apart a similar old Headshok a couple of years ago, will have rummage in my stash of crap to see what nick the insides were. I do remember it was basically knackered, I'd got it from Edinburgh Bike Station for a tenner just to get the Headshok headset cups that it had.
Have you had the fork off the bike? Just noticed in the pic of bike stripped down that top bearing in headset seems to be partially out of top headset cup.