One of the things I constantly struggle with is deciding where and when to spend the money. A universal truth in my life has always been that my desired efforts always exceed my existing means. This means I need to pick and choose where I spend money very carefully.
Some items are absolutely easy to manage DIY and they function just as effectively as the store bought ones. Other times there is a need to decide when to get quality and when to just get something that works. I tend to look at this in terms of hours spent using the item. If I'm going to spend hundreds of hours using something, investing in quality is far more economical than to buy the best of something I only plan to use a few hours a year.
What I really want to know is where other people have divided out their compromises. Where and when do you decide to buy the best? When have you decided DIY is just fine. Have you ever started on one end of the spectrum and found that the other side would do just as well. Buyer's regret on a big ticket item or realization that while you could DIY, it was much more taxing than just getting the right gear.
Speaking from my own experiences, I can say that a lot of DIY gear I've experienced got the job done, but always felt like a relief when I could get ahold of something a bit more refined. That's not to say it would be worth the money to get outside of a windfall, but still.
For me it often comes down to movement. Simple put, the more something moves, the more it breaks.
Three years ago now, I facd buying a very expensive implement for my bulldozer. I was not getting wood out of the woods because I was constantly breaking cables. The problem was I needed to get logs up off the ground and on tires. I looked into home made log loaders, but there was a ton of movement, geometry, and hyraulics. In the end I decided that while insanely expensive, ($18,000), the difficult engineering had been done for me. I also decided I could fabricate new implements to go on it, and if needed, to rebuild it and make it stronger. BUT I had something to build off from.
I have never regretted the purchase even though most implments I make myself. I use the machine every day, and its long paid for itself...in the first 6 months I owned it in fact. I have since builta feller buncher head for it, an upside down woodsplitter head, grader blade, etc. It is the swiss army knife of Homesteading. And I use it for farm more that just logging. Everything from breaking the beads on farm tractor tires, to putting siding on the house.
I use a simple formula for most purchases. I know how much I make an hour. I figure how long it will take me, and if my time is worth more than the cost to have someone else do it, I'll usually pay someone. There are exceptions of course. Some things I simply don't have the tools or knowledge to do. Those I have to bite the bullet on if I can't come up with a viable substitute. If it is something I enjoy, then I don't care how long it will take, I do it. There are other variables too. If you need something right now, it's probably going to cost you.
Tasks like using a saw or digging are more suited to machines while more dexterous tasks like picking fruit are more suited to animals or people. Weeding is more suitable to animals, while harvest crops from a messy field is better for people because all the left over weeds grasses and such can be trampled and returned to the ground via critters. Making tools and such is more suited manufacturers while raising cattle or planting a Garden is more suited to people. I would advise that you triple down or quadruple down on your talents and Outsource the things that you're not good at the people who are good at it and enjoy doing that task. This applies to owning renting land or managing the land for someone else if you want to get as big as possible as soon as you can. to start gardening soon as possible it might be better to talk to someone that already owns land and offering to start a garden with them in exchange for having the experience or another words doing it for free
I'm the guy who says "please look up allan savory, early retirement extreme, the wim hof method and permaculture" at any chance I get =P