Drew brings up another good point. With what you planning to do I believe you will need to think about a small pancake compressor and a nailgun.
I would say you need to consider this balance.
between you could go out and buy the furniture you wanting hand made from another woodworker and save yourself some money and time.
or you buy the tools the pro has to be able to make that long list yourself and in the process get to enjoy doing it, learn a lot, have a huge amount of fun and frustration at times and stand back and say, i made that and i have some new skills and i got satisfaction out of it. By then, i very much doubt you will part with those tools that easily.
This stuff is like a drug. Each step each swish or bang gets you more and more hooked. Once you smell the wood and get to recognise them and do a few joints that feel like an accomplishment, you suddenly start to notice them on other pieces in other peoples homes or at the furniture store or anywhere you find yourself. Next you start to examine pieces to see how they were made, you get drawn deeper into the vortex each step of the way. In some ways its not even voluntary. The tools well they just the facilitators almost like an orchestra with different instruments being conducted to play great music.
In the same way you will find a good musical instrument in an experienced hand can play a good tune so too will a good tool make the difference to the pleasure of what you want to achieve. A good pro can also make a poor tool perform but that takes years to achieve.
Do the sums Cynthia make a spreadsheet list on one colum all that you are going to need to make all the projects you want. Add the material for each even if its just rough estimates, include hardware because there are things where the wood becomes the cheap part. Include your tools you will need. You only need to buy them once for many projects. Tally up the colum.
Then pick and choose your projects, get some quotes to do them, tally that lot up. If you like leave out the projects you want to specifically do and already have the tools and lumber for.
See where the balance is.
Then you can take a view on what the enjoyment/learning/ frustration and time factor is going to be. You could even add to the bottom of the left hand colum a deduction for resale of the tools at the end if you want to be clinical. And if you want to be nit picky add in scrap because you will have scrap along the way thats part of learning even the pros create scrap mostly for test cuts and set up cuts.
Most of us here are committed. There is no justification economically for what we spend on tools. Maybe a guy like Alan or Chuck or Mike H or the many others that are pro woodworkers can get a return from their shops because they are experienced and way more productive due to experience than a hobbyist. You have an advantage that you seem to be at it on a semi permanent basis that will make you more productive and help the learning curve.
If you have doubts now do the spreadsheet carve yourself out some fun projects and evaluate where you wish to draw the line.
But remember when you compare using real wood to furniture you see in the store you are not comparing apples for apples.
I have a sucker buy dinning room table. My wife just had to have one when we arrived here. Its wood. But not the way it came off the trees.
Its probably mdf i cannot make it out without hacking into it, i know this because the chair arms certainly are. They used clever finishing techniques to make it look like some wood i dont know a dark cherry or whatever they call it finish. Did not fool me but satisfied Loml so what could i do.
If i had to build it from real wood, it would be way different to me. But few others realize this or appreciate the difference.
Its all your choice at the end of the day.
And there are always trade offs.
