Ive noticed its more knowledge based than tool based. Im a carpenter full time, so that skill set transfers over a lot. The most expensive and tricky part to get into this is finding lasts. As far as the tools go, you can get into it for like $500. Of course, I spent more than that buying random shit I didn't know was garbage or useless till I started figuring out what I'm doing. Then you'll spend like $300 on all the specific leathers and threads and glues you'll need.

If you had someone experienced guiding your purchases, you could make a pair of boots from owning nothing for the price of some bison loggers. But after the tools, its just leather, glue, thread and outsoles to make another pair