Sheeeit. I ask myself this every day.
I have a diverse mixture of old and new stuff. My tractors are all used, some of them from the early 70's. The new ones start at 225 and go up to 450 thousand. Way outta my price range.
The new and newish stuff still breaks down, just in sort of a different way. Might be covered under warranty, but you still lose time.
We bought our 4 wheelers new, horse trailers new, bale processer, baler, disc mower, post driver, v rake, and probably some other stuff I cant think of.
All three farming tractors were used, mowing tractor, four loader tractors, both combines, disk, both toolbars, air seeder, rock picker, couple of chore tractors, silly little Ford tractor, (impulse buy) augers, all three grain trucks, all four semi trucks, both dump trucks, both service trucks, grain trailers, all three hay trailers, D8, 950 loader, backhoe, compactor, road patrol, scrapers, excavator, both lowboys.
We dont do much dirt work any more, so that repair bill is quite low, but the parts bill on the rest of the lot is still lower than one years payment on a new combine.
We had to decide what we could get away with for new stuff. We cant be working on a baler when its time to bale, miss a day and the hay is almost ruined. We did pay cash for a used baler once, and worked on it all the time.
We had to borrow money for most of this stuff, but we could not have expanded like we did with out it. We dont necessarily see debt for capital purchases as a bad thing, as long as you keep it with in reason. Hardly anyone starts out with cash, just have to weigh the pros and cons.
Can we afford it? Can we afford to be with out it? How much labor will we save? Will it replace a hired man or make ours and his life better? Will the added productivity allow us to get our work done with room to expand? Will this let us spend more time with our family? Do we NEED it or want it?
Thats how we look at all our purchases, new or used.
I have the benefit of being able to fix all our stuff, as well as a hired man who was a mechanic for the National Guard for 25 plus years. That kind of ability lets us get by with older machinery. Not having that ability would cost us another 30 to 40 thousand a year. Plus being able to fix the old shit means I can buy two old tractors for the price of a newer one. We can at least have ONE running, or run both if we are lucky. So we take some chances on used stuff that would be silly for someone else.
You are lucky that you have been in the business for so long, you know what it takes to make it work. If you have the ability to work on your equipment, taking a chance on older stuff is okay. If not, the down time you might have could be devastating. You could VERY quickly have more into the machine in parts and labor than it is worth, or could make you in a long time.
I know it sucks to be in debt, but if you have a plan and a bank that will work for you, it is not the end of the world. We see it as a partnership. Kinda lopsided though!
If you can make the figures work, buy the best stuff you can afford. Dont hamstring yourself when you start out by buying junk, but if the numbers wont work, dont overbuy either. Also, it doesn't hurt to realistically anticipate expansion when making a purchase either.
Shit, that was a long winded post that was pretty short on actual information. Sorry. Good luck!