Lots of good stuff all mixed together in this thread, since the original post called out a lot of common wisdom and challenged it. Bravo! This is part of what makes this community so valuable.
Let me however challenge back a bit on the premise that hobbyists in particular are too quick (or are encouraged too often) to buy more than they need. I think that's sometimes true, especially when spending too much extra $ before they know what they really need, and then not having the $ to get the extras (e.g. additional implements) that would actually make a real difference once they figure it out.
However, not always. It's important to recognize some hobbyists are constrained as much by time as by cash, if not more. Yes, for many, saving 2 hours total mowing time per year because of a bit more HP, or turning a day maintaining the driveway into 2 hours with the right implement, is a frankly unnecessary luxury. It's all fun seat time anyway, they have loads of time to do stuff, and if a few more projects end up being pushed to next year, it really doesn't matter.
For others, whether due to the time demands of their "real" job or family responsibilities, or just because they're fond of setting ambitious objectives for themselves, it's always a race against time. Faster mowing time and driveway maintenance means they'll actually get around to fixing that old culvert before it floods the road. Having the right gear to pull stumps on the new pasture a bit quicker means they'll actually have the time "left over" to prune the new plum trees in the orchard the way they deserve. Or won't give up on that pasture in frustration for the 3rd year in a row. In contrast, saving money by getting the wrong (underpowered) equipment will cost $ and time if they decide to upgrade later. And cheaping out on gear that ends up breaking right at the beginning of your 2 weeks scheduled time off (to work on your land) doesn't mean you shrug your shoulders and do something else while waiting for your machine to be fixed, it means you postpone your Big Project to next year, or run around madly spending any amount of $ renting a replacement, because that's your one chance.
I got lots of good advice on this board a few years ago when I was starting from scratch, and I took the various comments phrased as "you should really get extra X and Y" not as "you'd be dumb not to get ALL of this extra stuff and blow your budget to smithereens" just as "be sure you think through what X and Y (and A and B and C and ...) might bring you, 'cause you might have missed their advantages."
I overbought on some things, I underbought on others. My main trailer is needlessly large and beefy. I could have bought a crappy old boxblade rather than a shiny new one. On the other hand, every time I have to downshift on That One Hill to low from medium range, I regret I didn't get those extra 5 HP. And I've just spent real $$$ buying an new miniex post-COVID when I could have spent $ buying a new or used one pre-COVID, had I paid more attention to those telling me a tractor backhoe has real limitations. I'm not mad - you win some bets and lose others - but this time vs $ tradeoff can get really complicated.