I often get asked about initial outfitting of the shop with stationary or powered tools. If I were begin again from scratch today, this is how I would proceed.
My first purchase would be a stationary table saw (contractor or cabinet) with at least a 2 hp belt driven motor. The 2hp is necessary for powering through thick stock or using dado blades, the heaviness of a stationary tool and the belt driven motor help reduce vibration and give you better cuts. I would also find a saw with a cast iron table and a riving knife. This single tool is probably the most versatile and central to a modern woodworking shop. Sometimes the blade you get with the machine is good but often it is a general purpose. I would probably splurge for a good quality plywood blade as plywood is also pretty central to my woodworking. Make sure not to cut cost corners on this purchase. Often you can get good deals on used machinery and tune them up yourself.
My next purchase is tied between a drill/driver and a router. There are very good handtools that can do either of these functions but powering these actions can really speed up what would be pretty mundane tasks. When getting a router, get at least a 2 hp router with the ability to change the collet size. The 2hp is essential because you really don’t want a boggy router because it slows feed rate and increases burn. Cleaning up a burned routed edge is a nightmare. That being said, having good bits is also essential. At the very least get carbide bits. If you can afford it, get top quality carbide bits and in the biggest shank size you can fit in your router because this will reduce your vibration and clean up results better. Good router bits are expensive but they are worth the extra money IMO for quality, expected life, and results. I would probably recommend getting a large router bit collection unless you know for sure what your style of woodworking will require. You also might consider a router table at this point as well, depending on what you are doing.
My next purchase would probably be a random orbit sander. Make sure to pick up some masks at the same time and a good selection of sanding disks. Who likes sanding by hand? Enough said.
Next purchase would be a stationary bandsaw. I would recommend researching what you intend to use it for before deciding what to buy. Again, deals can be found with used tools. If you are planning on doing fine work and not much resawing you can save some money and get a slightly underpowered 14″ 3/4hp bandsaw. If you are going to be doing resawing and a lot of it, definitely consider a larger saw with a lot more power. Think 2hp or more. I have a 14in 3/4hp bandsaw and I can only resaw wood up to about 3 in without bogging down. I however, have no problem with sawing normal curves in normally thick stock. I’ll add a caveat at this point. A lot of the functions you can do with a table saw can be done on a bandsaw although feed rate is generally slower. If you want to saw a lot of curves, maybe consider a bandsaw first. You also might want to consider a scroll saw here if your interest is in small detailed work. The feed rate is incredibly slow so don’t think you can saw 2x4s on a scroll saw.
Depending on how much you deal with sheet goods, a circular saw might be in order. Stick with the reputable brands on this one and you will love yourself for it later on. Sheet goods are heavy. Instead of trying to hoist up a whole sheet to the table saw and try to get an accurate cut, I cut all my panels oversized and then trim to spec on the table saw when they are more manageable. A neat trick I use to cut plywood anywhere without worry of hitting something with the blade underneath is to get a 1in thick sheet of foam insulation- the hard pink stuff. I set my blade to just nick the surface of the insulation. I can easily cut plywood in the middle of the table by myself without worrying about supporting the cutoff. I use a 90degree angled piece of aluminum from the local home improvement store and clamp it down as a track. Super cheap and lightweight. Circular saws are handy in general around the house.
Perhaps the next thing I would buy is a drill press, used if possible. The precision you get compared to a hand drill is remarkable. Get a floor standing one, used if possible. The ability to change speeds with a turn of a knob is overrated IMO. I use two speeds and it’s not that hard to switch. Drill presses are great for hole drilling using forstner bits.
I would buy a compound miter saw next. This is a non essential tool but ever so nice. It’s fast, accurate, and I probably use it the most. But on a shoestring budget, I would make do for a while unless you are doing crazy angles for crown moulding. You could probably with a little practice still get by on the table saw.
I you are going to deal with roughsawn lumber you may want to consider getting a jointer and a planer at the same time. I would recommend against getting anything less than an 8″ jointer, larger if you can wing it really helps with long stock. The portable planers on the market are actually quite nice and give great results. They are much cheaper than stationary tools. Unless you are doing high production requiring lots of planing, I would stick with the portable planer.
Other tools to think about are a biscuit joiner, drum sander, and a vacuum press. None of these are essential but can be really nice. Each person’s shop is different.