Glad you and Pa got the okay from the bosses to get some toys, I mean tools.
When you start putting your shop together, don't just start buying tools at random. First thing you should do, is something most guys never think of.
1) Ask yourselves what types of woodworking you will be doing most. It can evolve and usually does but it's an important first step. For example, if you know you want to build mostly cabinets at first, then you know you will need . . . . LOTS OF CLAMPS. You thought I was going to say a table saw didn't you?
I am, but it's obvious so I thought I'd make tyou aware of an expense most guys don't figure in to the budget. Clamps are expensive, and I keep an eye our on craigslist frequently and snatch up good deals when I can. The goal is to have 1000 clamps of various sizes and flavors. One hundred will suffice though. That's everything from spring clamps to bar clamps and ratchet clamps etc.
Another example why it's an important question is let's say you and your dad already know you want to make a bunch of whirly gigs, bird houses, and all manner of that kind of artsy crafty stuff. If you know you won't be doing much or any panel work, you need a good bandsaw more than a table saw in this scenario. You could get by just fine without a table saw in this case and just purchase a sub-$100 guide rail system for your circular saw. I can't imagine a woodshop without a table saw, but I can see how a benchtop tablesaw would be all a small arts and crafts shop might need, and just take the $1000 you would have spent on a behemoth cabinet saw and buy clamps and more clamps.
If you ARE going to be doing a lot of panel breakdown and little to no resawing solid stock or cutting small curvy parts, then you could get by without a bandsaw for now and just buy a nice jigsaw.
You'll need a planer. period. You need a good block plane. I would be lost without my little Stanley 12-220 block plane. i love that cheap little bugger. Most will tell you that you'll need a jointer. That's true if you are going to be making a lot of highly precise projects with thin stock. A planer bed will not give you a flat side on thinner stock because the rollers will push the stock downward, and it will bow back up as it comes out. So add a jointer if you are going to be building nice jewelry boxes and humidors and fine furniture.
No matter what type of woodworking you and dad delve into, you are going to need a good router or two, and a router table is always nice. A random orbital sander, belt sander (benchtops are nice) and a drill press. It can be used for lots of cool things.
2) After you make a list, and have crossed out about 25 things because you had no idea how expensive putting a shop together would be, look at what's left. Now it's time to shop. How do you know which tool to buy? Should I buy all one brand? NO!
IMHO, buying tools from one manufacturer is a mistake, because you rob yourself of owning the best tools in each category. For example, if I bought nothing but DeWalt tools, I would not have looked at the Bosch European barrel design jigsaw which, at the time was hands down the best jigsaw on the market.
If I was shopping now, I'd take a hard look at Festool if I knew I was going to use a jigsaw a lot. If I wasn't might not be able to justify that much money on a tool I'd only use a couple times a year. In that case, buy the best, highest-rated jigsaw in the dollar range you can afford.
amazon.com is an excellent source to read tool reviews. They are USER reviews and I always put more stock in those than edipor reviews. This and other forums is also a great place to read tool reviews
There' much more to putting a shop together than this, but I have to get out of here and get something else done today. This is a good start and others will hopefully fill in my large gaps.
P.S. Don't forget a good dust collection system in the budget.