I'll add my $0.02 here (some of it's repetitive). I'm in a similar position as you, only 4 months down the road give or take. Not enough to give you much real world insight. I also have a similar mindset when it comes to tools, hobbies, etc.
I have a dewalt contractors table saw. I know what can go wrong using a saw, I try to be safe, but at the end of the day, I'd rather minimize the time the table saw and I spend together. I haven't parted with it yet, but my goal is to make do with the track saw, MFT and some aftermarket accessories that make repetitive cuts simpler and more precise. No matter what I do, it won't be as convenient as a table saw, but I think I'll do okay if I force myself to use the table saw as a last alternative. My issue with the sawstop is I'm unwilling to sacrifice garage space for it and I'm concerned about dust in the basement. Right now my portable saw comes out from the basement and gets set up in the driveway or back yard. That's not happening with the sawstop. In your case I would try something similar. Keep the existing table saw and see how you make out with the track saw. Go from there.
Dust extraction - as said, that is the heart of their tools. You don't have to use their "vacuum". A fein could be had for half the price. For some reason round barrel shaped shop vacs irritate me. I think it's because I spent much of my childhood picking up a tipped over craftsman vac with a rigid 5 ft hose on it and it's scared me for life? I digress, that's my problem not yours! I like the form factor of the festool (rectangular and stable so it never tips and stores neatly among boxes, systainers and other stuff in my basement) and the ability to lock systainers right on top and roll the trolley about as needed. I have a number of things in my basement that are mounted on wheels so I can move things around quickly depending on what I need space to do. The CT26 is a nice blend of capacity and size, however many use a midi or mini with a cyclonic collector which traps the bulk of the debris. Your choice on which way to go.
The next star in their line up are their sanders. Eventually you'll find a need for more than one, so buy based on the tasks at hand. Finish sanding, ETS, detail sanding, RO90, heavy restoration work, RO150. I'm not really inclined to look outside of Festool's family here. Most seem to get an RO150 and RO90 I've noticed. I chose the ETS150 (because it's easier to manage and I don't have a need for heavy removal) and RO90 myself.
If you're doing joinery, a domino is really cool. Very few equals to this one. You must have some kind of dust extraction for this. It's almost too cool not to have! 
Miter saw - Kapex. I had a chance to fondle one last weekend at ToolNut. I already have a 12" saw so it's a tough pill to swallow for me. I absolutely loved how well everything worked on this saw. Precise, ergonomic, exactly what I expect to find when I pick up german made machinery. My only critique is the stiffness of the miter table (I'd like to put this thing on ball bearings!), but I could live with that. I'll ponder whether I'm willing to trade capacity for precision and unparalleled dust extraction. I'd much prefer to do crown and base cutting against the fence and the kapex will force me to cut flat. To me that's a big deal. I wish I could borrow one and force myself to use it for my next trim project. Unfortunately their 30 day trial just isn't enough for me, unless I really block out a few weekends, which I can't do now.
Jigsaw - when you have a need for one, check out the Bosch saws as well. They are quite nice, though the top of the line are not much cheaper than a Festool. I don't think the dust extraction with the Festool is any better or worse than the bosch.
Drills and impact drivers - I already have a 12V and 18V set from Bosch and Makita. On the 18V system, I have several cordless tools all using that battery system, so I doubt I would switch to Festool. If I was buying from scratch, I'd probably still look at Milwaukee and Makita because of their extensive line of cordless tools. For a hobbiest and homeowner, that versatility is helpful. Ryobi has also released an interesting mix of cordless tools lately. I know, not a name that you want to say out loud in the company of FOGer's, but I think they've become a real alternative to some of the brands carried in box stores. Back to festool, if you're working in tight quarters or cabinets, the CSX is one to consider. Or the larger C12 with their eccentric chuck. That's really cool! Not domino cool, but....
Two things I will leave you with...look at Festools bundle deals. You save 10% off an MFT or extractor when buying another power tool. If you plan your purchases, you can save a bit. I didn't look at all of them to map out the purchases, but then again, when I made that first purchase, I didn't realize where this was going. The tracksaw and extractor combo got me hooked! You've been warned, but I suspect you already know yourself all too well, so you know where this is headed. Finally, if it helps for planning purposes, I usually double the purchase price of a power tool. Invariably the cost of consumables or accessories (neither of which come cheap) will add up. Now I just add that into the budget and hold off until I can get the tool with everything I want or need with it, otherwise I feel like a kid at xmas without batteries for his toys! Sometimes double isn't enough though. I got a 1400 router, now I want (need?) a CMS table. A set. That's gonna hurt. Only once. It's only money.
Enjoy and Welcome to the FOG!