First off, make sure you allocate some money for accessories and what-not. They're not cheap, and its amazing how it all adds up. I'd say set aside $500 in your budget for clamps, paper, blades, bits, etc etc etc. (hehe once you taste Systainers you want to put everything in them!)
Second, I disagree about the Kapex. If you do find yourself needing a miter saw, make sure you need a slider. Not many furniture items require that kind of cross cut capacity, and simpler quality CMS units can be found for less than $200. If you decide you do need a slider, there are several models which are equally as capable and well made and have decent dust collection. I use a Bosch 4410, mounted on a Ridgid MSUV (old style, yeah!) and together that cost less than half of a Kapex. With a 36mm hose and my CT, it is a fairly clean operator. Sure, it doesn't have rack and pinion bevel setting, nor the cool miter device (I use something else) but it does any/everything I demand of it.
Use that $1100+ towards *several* other tools
Okay, the starting purchases question has a very common answer: TS55 and a CT. Bang, you're in the water with both feet, and well equipped for to expand "the system".
A few further suggestions on this: Upgrade your TS55 purchase to include either a LR32 55" rail, or bump up to the 75" rail size. You can always get a smaller rail later, but having a longer one is rarely problematic. You will eventually get more rails... it's a guarantee. Also, I would strongly examine your expected use, in terms of location. If you'll always be in your shop, the CT36 is only $50 more than the CT26, and you get a lot more volume in the 36. Along this line, I would recommend get a 26/36, rather than the 22/33.
And finally, upgrade to the 36mm hose with your CT. The 36mm hose is eminently more robust and works with almost all the tools. You can get an adapter for about $50 to go with the certain tools that require the small hose end. You can use the 36mm to do shop cleanup. I find the 27mm hose clogs with small/tiny offcuts and even leaves (part of my shop is the garage).
So, there goes roughly $1100. (You will think this stings, until you fire it up)
You can now cut and clean up. Next would be shaping and heading for the finish line.
The OF1400 is widely considered the ultimate versatile router. There ya go. If you don't already have money invested in 1/2" shank bits, you could consider the OF1010. But for that $100 discount you are closing off a big marketplace of router bits. Search around and you will find plenty of lively debate about the two routers.
Sanders: This is a toughie, as Festool offers so many sanders, and they're all awesome... And you also need to factor in consummables and having different sizes and grits to buy and store, etc.
Take a hard look at the Rotex models. You mentioned your hand size may have influence. A side benefit of the 150mm size is the nice hand sanding blocks you can get, but they should not be a deal breaker if the 125 size is better for you.
If you are
not going to be working rough stock (e.g. not much need for the rotary sanding), then consider the ETS and DTS. You can get them
both for less than the price of the Rotex 150.
As you round the turn, there's another $1000 (you'll need to get some sandpaper, probably the router rail guide stop, and some other goodies).
Finally, the Domino. Hands down, if you plan to make furniture this is a tool you want in your shop. If you are truly brand new to wood working you might not ever fully appreciate how sweet this thing is, and how much time it saves, and how fantastic and precise the results are. But, even if you don't know what you're missing (e.g. tedium) you'll appreciate the final results. Again, factor in some funds for accessories. Pony up for the Domino assortment set (which includes all cutters) and you're basically set for life. Or get them one-by-one as you need them.. either way, you might likely end up with them all. [embarassed]
Bon voyage! The ride on the slope IS fun!
PS: San Diego and Washington, huh? Check out
www.searchtempest.com A Craigslist search aggregator. There are Festool bargains to be found. But carefully weigh any (sometimes minor) savings vs. new, full warranty, and 30 day guarantee.