expensive CP995 housing or new camera w/ cheaper housing?

For a few years, I've been using an Ikelite Aquashot 3 housing (this is the one that takes disposable film cameras). It's fun to play with and occasionally you get something worth putting in a frame (see here for one half-decent shot I got with the macro kit). I'd like to make the jump to digital, but I'm not sure what equipment to buy. Elsewhere on this site, James Wiseman has an article (2002) where he suggests either the Nikon Coolpix 995 or an Olympus model as good cameras to start with. As it turns out, I already have a CP995. I'm also planning to buy a more compact digital camera that I can use, at least in part, above water on occasions when the CP995 is just a too bulky.

So my question for the friendly experts out there: should I buy a ~$750 Ikelite housing for my CP995, and then any model I want for the 2nd above-water camera? Or should I look for an Olympus or Canon model (compatible with a ~$200 housing) that can double as a more compact above-water camera? Or do you suggest something different all together? I guess I'll need to get a strobe in either case, as I don't think that my light-triggered, unadjustable Aquashot strobe is good for much else than its intended purpose. As for my budget, I usually go on one week-long dive trip a year, so I don't want to sink $5000 into a system. On the other hand, this is for fun, so I'd rather have a system I really enjoy than save $200 on a system that's going to annoy me.

Thanks for any suggestions.

--Josh