A pillar drill is never going to be your only drill, it's an addition and compliment to the standard handheld tools. If you can fit something under a pillar drill it'll often be the best choice, but for a lot of larger projects that's often not possible. Especially for the bigger types of wood you'll still be going to the handheld tool. However, for things like drilling holes in hinges, reinforcing plates or brackets that are awkward to hold down while using a handheld drill the pillar drill is absolutely a nice tool to have. Do you absolutely NEED one? No, not really. But I've missed not having mine set up right now on multiple occasions.
At 2ft wide, to drill the holes in your proposed stocks you'd need a pillar drill with about a foot of clearance from the centerline of the chuck to the front of the column. Most home shop size pillar drills are not going to be able to fit that (The technical term for the measurement you are looking for in that regard is "throat depth" btw). My dream shop would contain one of
these little beauties (Warning, serious risk to the health of your wallet going to that site). They have some very nice toys for sale... (NO, BAD Gregovic, NO
Don't even THINK about it
)
If your looking to rip large boards, a "contractor" size table saw isn't really going to do you much good. It can be done if you just need strips that are narrow enough that you can still install the fence, but you need a friend/helper and a lot of patience. Basically anything wider than the table width either side of the saw is going to be impossible on a smaller size table saw. Generally I just get my stuff sawed at the DIY store where I buy so it's in sizes that I can actually handle and work from there.
Apart from the power tools, have a look at buying a good set of hand tools. Things like hand saws, chisels, planes, screwdrivers, scrapers, knives, etc. While power tools certainly have their place, I find I can often do a lot with just a simpel chisel, a scraper or a hand saw. Especially a good quality hand saw (I have good experience with Sandvik saws) can make short work of a lot of things and can often beat getting a power tool out, setting it up and making a cut, at the cost of a little sweat and elbow grease. For things like smoothing out joins or plugs a good bench plane or block plane are tools I sorely miss having. Even for the little carpentry I actually do.
When it comes to battery drills, if I was looking again now I'd probably buy something with a brushless motor. While the Bosch Professional drill (GSR18-2-LI) that I have has lasted me for 3 years and some heavy use during remodelling my house it just gave up this afternoon. I suspect the brushes have worn out, but they are not replaceable and a new motor is €60,- and requires re-soldering wires. I'm not sure I'll be doing that. A brushless drill should at the very least not suffer from degraded performance as the brushes and commutator wear out. My next one will probably be a Makita, as I've used those before and I like the finish and handling of them.
BTW, if you ever experienced the annoyance of having to switch between 2 tools in the drill (like 2 drill sizes, or a drill and a screw bit) and you inadvertently find yourself in an Ikea in a moment of sheer madness, pick yourself up one of these cheapish
Fixa battery screwdrivers. They're not powerful enough or fast enough to serve as a main tool, but they're ideal to have around as a backup and secondary tool for those days when you keep having to switch.