Al (from RAW) may do a custom sub kit for you depending on your requirements. Email him with your request (info@rawacoustics.com) and when he is back form holidays I am sure he will disucss it with you.
As for any of the other kits, I would start with the smaller speakers, like the HT2 or even the RAW FR.
What is your intended use?
I'd like to work my way up have a set of 2 channel floor standing speakers for audio (jazz, vocals, etc) as I upgrade my audio setup. My original thought was to get a 2nd hand set of Mirage M3s (or similar). I'm now considering going the DIY route, but I think if I go this way, starting with something manageable would be best.
I could do with a better subwoofer for my HT setup --- which is why I thought of the subwoofer. It's also tucked away, so any, err, "learning experiences" would not be so visible

I'm not sure what I'd do with the HT2s or RAW FRs when I was done.
PS Your guitars look wonderful.