It helps me that my grandfather is a life long clock maker.
It also helps me that my wife has known me to get into 100+ hobbies (some advanced, some not) in our 6 years so far. Beer making, ships in a bottle, distilling, model building, winemaking, coin collecting, fire breathing, fire eating, tattooing, book binding, cinematography, film developing, camera making, and of course clocks.
The three big ones that have stuck for me are clocks, tattooing, and wine/beer/distilling.
So I usually start off by purchasing smaller items here and there. The only big things I’ve ever needed are for the clocks, tattooing, or alcohol. She’s usually cool with the big purchase as long as she knows I’m not going to let it sit and collect dust.
For the clocks, I started playing with junk. Ordered a pile of junk off eBay, bought a few piles of junk on craigslist, and just played with them for a while with basic hand tools until I got it all down. I didn’t feel like I should spend much on tools at first. So for a let down, I just matched a near-sized socket up to the winding arbor with a screwdriver attachment to let springs down.
Fortunately, my grandfather has given me a lot of tools. Most of the tools are basic and don’t cost much, but they all add up. That’s not to say I haven’t spent a lot of money ordering tools.
Unfortunately, I got into this about 2 years too late after my grandfather quit working on watches. He sold all of his watchmaking equipment on eBay for about $3,500. He told me recently he would have just given it to me if he would have known.
. . . Now I need a lathe. Looking to buy one.