When you took up a new sport hobby with expensive equipment, when did you decide to buy rather than rent it?

Fly fishing I borrowed equipment first, then got what I needed.

Mountain biking I purchased a mid-quality bike and related gear. I have since upgraded many times but always buy used frames

Golf. I rented the clubs at first. Then I pared my first hole, and I decided to get more serious. Then I fing tore my rotator cuff, twice a few years ago. But I’m thinking of giving it a go again.

Kayaking. I went out three times in rented boats before I bought my own kayak and paddle. I bought what I thought I would be satisfied with for several years, but that was two years ago and I’m already itching to upgrade.

Snowshoeing. I bought right away because the rental price is high enough and the cost of the equipment low enough that they pay for themselves after less than a week of daily use. I discovered almost right off that I want a different pair, but that’s ok because my initial pair were fairly cheap and I can probably sell them without much trouble.

I own my own set of skis and I used to own my own scuba diving equipment.

In general I am quite quick to buy my own equipment, because I like gadgets.

Skiing. When I skied more than three days a season.

The first few times, I usually rent, or make do with something similar that I already have (depending on the activity, sometimes you can do this). Then, if I think that (a) I’m going to enjoy this activity, (b) I have a chance to do this with some regularity, and ( c) I can get reasonably good at it, I will buy. The advantage to having your own equipment is that you get it customized to your body size and to your level of expertise. There is something of a vicious cycle in this. The better your equipment fits and suits you, the more you’ll enjoy the activity, and the faster you’ll get better at it. Then when your level of expertise increases, you’ll be ready for yet another round of equipment buying.
As for buying what you need or what you hope to grow into, I would aim for something just a bit beyond your current level of expertise. That will get you to that level sooner.
Take skiing, for example. If you’re a solid intermediate skier, you should buy beginning advanced skis (that is, skis for advanced but not expert level).

Another advantage to having your own equipment is convenience. You don’t have to stop at the rental shop before and after, and you don’t have to worry about their running out of your size. So, how often you plan to do the activity is an important consideration.

Thanks. Keep em coming.