For me, the things that have made the most difference are the items that offered huge QOL improvements but were an enormous upfront cost – purchases that I put off purchasing for years, sometimes even decades… Why did I do that to myself?!
My Hayhut. It has made life so much easier. No more schlepping out 6x a day with hay, cleaning up dozens of little haypiles in the paddock every other day, no having to cover the roundbale every time it rains (and in the NE in the fall, it seems to rain constantly).
My Haychix Haynet for the round bale + Hayhut. I admit when I first read claims on this forum that a Hayhut + Haychix haynet eliminated 100% of hay waste I figured it was generous hyperbole. It’s not. Before the haynet, I was probably losing 1/3 of the bale to waste. It meant the paddocks got awfully soupy and you couldn’t place a roundbale in the same spot - when you’re putting out one round bale every 5 days, you would be amazed at how quickly you run out of room and how quickly hay waste adds up. I used to have to go in with a skidsteer and pull out bucketloads of wasted hay. Now, I only need to go in with the skidsteer for a quick pass once a month, if even that. The horses might waste a few flakes worth of hay, but nothing like it was before the haynet.
My expensive Kingston trailer with dressing room. I traveled for years out of a stock trailer with no dressing room. Never again! I still feel like it’s Christmas morning when I use that thing and have the luxury of pulling my saddle out of the dressing room instead of having to dig through the back of the truck.
My AA MotionLite Coat. It was expensive but the fabric is breathable and flattering.
And finally… the Rambo/Rhino rainsheets the herd is outfitted in. This was an enormous cost to swap all of the herd to them, but the quality and peace of mind I get from knowing they’re dry and warm is worth it. I was going through new blankets at the end of every season until I swapped to Rambos.
Things that I did not get my money’s worth out of were the Tredstep Donatellos and Shockehmoehle Equitus Alpha bridle. Both fell apart within fewer than a dozen uses.