If you are building a shop, the two power tools that could basically build a whole boat are the hand drill and the jig saw. I kid you not. Almost 95% of the work is with these two tools or can be achieved by these two tools and a long t-square. Everything else just helps with the other 5%. These two you probably already have. Every year or so for the last 15 years I have tried to get one nice tool, either a large power tool or a nice hand tool. Only the bandsaw was a used tool.
As for the drill press, I have a Delta. I picked it up at Lowes along with a Delta jointer, after working them down to $350 for the pair. I figure the deal was worth about $700+ as they were both floor models. I then sold the jointer since I really don't use one and almost covered my cost. So it was just about free. Maybe some day if I build cabinets or something I will pick up another jointer.
Here are a few brands I like, and in the order I like them. Maybe the list is helpful if you are looking for additional tools.
For large power tools: Powermatic (table saw), Robert Sorby (lathe), JessEm (router table w/Portercable 3.25), Jet (bandsaw), Delta (drill press), Delta (vac system). I picked up a slide for my table saw that is made by JessEm but I really don't have room in the garage to install it. It was such a good deal I could not pass it up. Hopefully when we move again I will have room for the slide.
I saw the vac system in your shed. It's perfect for the job! I have a similar Ridgid, but older. Those are perfect for boat building.
Most of the fine cutting tools are Bosch, and the more rough stuff is the Ridgid (drills, sawzall). Some Porter-Cable, I recently picked up a Makita hand planer for working on the boat, because it had really good reviews. I like reviews, and I try to avoid making a decision off of just the best deal. I also like Milwaukee but don't own any. I have had a few Hilit's in the past they are amazing (hammer drill, hand drill, lasers).
For power hand tools, I own Bosch, Porter Cable, Ridgid, Dewalt and a few more that I can't recall. I got rid of most of my old Dewalt, because it just gave up the ghost. Mostly battery powered tools. I imagine the newer generation of Dewalt are great.
Some brands really excel in one area (i.e. Dewalt with miter saws) and others in another (Porter-Cable 3.25 fixed base router motor). So try to avoid brand allegiance, but select the best tool for the job. Even consider Harbor Freight if it is a tool you will only use maybe 3 times in your life, or if you know the task will destroy the tool.
Hope this helps!