Newcomer prioritizing shop tasks

[MechanicalHg]

I find myself moving from project to project without taking the time to develop my Shop layout based on my workflow. I've mainly built painted or polyurethaned bookshelves, tables, step stools (and even a helper tower a-la the WoodWhisperer) for the kids but want to move into small items for easy gifts like boxes, picture frames that I can improve my finishing skill on. I think my ultimate goal would be to sell some items to earn back some of the money I've invested into the hobby. Implied in the fact I have kids < 3 years old is the fact I will not be devoting more than $1000/year on this hobby.

Any tips on prioritizing tasks for a newcomer still managing things ad-hoc without a dedicated layout?
For builds should I focus on making proper dust collection first for safety purposes, or jigs that get me reliable cuts, or the mainstays of the shop like a solid workbench?
For tools should I save up money for a drill press or can I get away with a DIY version that can get me perpendicular holes every time?
How do I get better at finishing projects? What surface prep method do you swear by to get mirror-smooth finishes? My wife loves the repurposed oak table I built but all I focus on are the imperfections.

Experience:
Mostly working with pine, oak, poplar, and MDF from the big box stores so far so nothing exotic. Haven't had the guts to venture to a local hardwood dealer, though I've heard the markup and quality at the box stores are horrendous by comparison. No experience with shellacs or varnishes yet, primarily because I don't want my kids exposed to the harsh stuff in the house since the shop is right below my living room. Even working on things for the shop would increase my skill level to where I'd feel comfortable gifting things, which is why I wonder if making a DIY drill press or router lift wouldn't be such a bad idea.

Space:
Basement is 12' x 24', uneven concrete floor requiring me to shim the platform I've devised for the tablesaw. 7 ft tall ceilings. Humidity varies widely throughout the year since it's the basement of an old house, so I always have to account for seasonal wood movement.

Tools:
10" DeWalt jobsite compact Table saw, 1 HP 1/4" collet Craftsman Router with basic Router table, Corded Power/Hammer Drill, Jigsaw, 5" Random Orbit Sander, Hand chisels, Kreg Pocket Hole jig, Dremel, ShopVac, 3' and 6' straight edge clamps, Harbor Freight 6" F style, 24" bar, and 2" spring clamps. Oh and a useless Stanley No. 3 handplane that doesn't keep the iron from shifting even after one pass.

Tool Wish List:
Drill Press, Bandsaw, Planer

Shop To-Do List:
Workbench with a vice and storage, Tablesaw outfeed table, Dust Collector, Sharpening Station (sandpaper on flat plate - scary sharp method), Stock organization for sheets, boards, scraps.
Small things like: Miter sled, Marking gauge

Thanks for any guidance, encouragement, or suggestions you have. I'll post some pictures of my work sometime.

[Chet]

27 minutes ago, Mike. said:

A jointer and planer are two different machines that perform two very different tasks.  

And you need the jointer to get proper results from the planer and you will need them both when you start buying from you local hardwood dealer.

Its been mentioned here in the past but some times it pays to keep an eye on your local Craigslist for some of the power tools on your wishlist.

[drzaius]

Sorry, I can't do your poll because there is no a single answer to those questions, at least the first 2.

For the third, I think just a very basic workbench would be a priority. It doesn't need to cost much or take long to build, but you need something to build stuff on

[Beechwood Chip]

1) I've made stuff with just a circular saw, shop-mate portable workbench, clamps, a straight edge, and wood or MDF to make jigs and guides.  Next priority is a hand drill, followed by a router.    After that, only buy the tools that you need for your next project.  Unless your hobby is "collecting cool woodworking tools" as opposed to "wood working".  Which is fine - When I was a kid I collected cool fishing tackle but never went fishing.

2)  Whatever Marc recommended in "A Simple Varnish Finish".

3) Just build something.

I couldn't do the poll because question (1) was required.

[wareaglewoodworker]

20 minutes ago, Beechwood Chip said:

2)  Whatever Marc recommended in "A Simple Varnish Finish".

I second this.  That's the first TWW guild project I bought.  Come to think of it... that's how I found this crazy community in the first place.  Hard to believe it's been 1 year, 3 projects, and 291 Wood Talk episodes since I went looking online for advice on finishing. 

[wtnhighlander]

Can't do the poll, because Tapatalk doesn't show them, and I'm too lazy to switch over to web view.

Unless you want to switch to hand tools, and assuming your shop is a full basement, I suggest dust collection as a priority. I would also suggest an inexpensive benchtop drill press over a jig for the hand drill. Otherwise, you have a good set of tools to start with, outside of milling lumber to be flat & square. The less expensive route there would be a decent jack plane and lots of practice. If you look closely, you will notice a lot of that very expensive box store lumber needs flattening, anyway. Also, set aside money for better quality sandpaper. Amazing how much difference it makes.

[Coop]

You've opened a six pack or more of worm cans in one post!

[..Kev]

If you're going to be primarily a "power tool" shop, you should have the basics.

Table saw, jointer, planer, plunge router, and sander

From there, you can move to the next tier of tools that really make your life easier

Band saw, drill press, miter saw, router table, dust collection, and drum sander

Once you have a shop full of basics and have done some projects, you'll get a better feel for what kind of projects you like to do and what direction you're heading in.  That knowledge will drive all the other purchases.

[PeteJr]

When I began woodworking I started with a Tablesaw and a Drill Press.  The shop I purchased wood from planed the boards and jointed one side.  Worked like this for a few years then bought a jointer and bandsaw.  

[Eric.]

There's way too much in that post to unpack even a fraction of it.  Take one bite, chew it, swallow it.  Like Chip said, just build something.  Your shop and skills will evolve over time.

Pick a project that challenges you but isn't way beyond your abilities.  You'll develop new skills.  If you need a tool to complete that project, buy it.  You'll grow your tool collection.  If you find some inefficiency in your workflow, address it...move things around or change your process.

Suck it up, go to the hardwood dealer, buy some cherry.  It's nice quality hardwood but it's not so expensive you'll get suicidal if you make a mistake.  You'll find yourself more comfortable working with more costly materials in no time.

Keep in mind, you never stop growing your skill set or refining your workflow.  It doesn't happen overnight.

[TerryMcK]

If you want to read something during the cold winter have a look at "Setting Up Shop: The Practical Guide to Designing and Building Your Dream Shop" by Sandor Nagyszalanczy. It does what it says on the tin