I’ve definitely come a long way since I started with leather about 4 years ago. Like others have said, I’d say it really is based on your personal preference for tools and what you’re doing. I still have a long way to learn about craft and tools. But Ive gotten to a point where I want to put some more money into tools that can be helpful and make the work a little easier. It’s starting to seem more worth it 4 years later. I’m also pretty frugal with not wanting to spend more than I’ve needed.
That being said, I’d really suggest for you to go buy a bag of scrap leather from hobby lobby and Micheal’s, or other places (those seem to be easily accessible). They have some good pieces to make simple projects out of and are about $6 with coupons.
Honestly, if you’re just wanting to try your hand at it some, I think some good things to start with at something to cut with (a box cutter, rotary cutter, dedicated leather blade), rubber/contact cement, some pricking irons and awl or chisels for stitching holes, a hole punch (rotary or individual punches are pretty cheap), thread, a straight edge/ruler are really all you need to make some simple projects. And all of them you can get for under $50. Amazon has some pretty decent cheap kits that will definitely get the job done for now. And if you want to progress more, as this thread has shown, there’s lots of tools and ways to get the job done if you enjoy it enough!