I think a lot of the time, the question boils down to "Get the best, or get something that works well enough." Occasionally, you will actually have a NEED for "the best" and in that case, you'd best get the best and what you need. Most of the time, though, there is usually something SIGNIFICANTLY cheaper than "the best" that does the job you need it to do, just perfectly fine, plenty good enough, and it will work for plenty of years (maybe even decades), for...1/10th the cost? Or even less (say used)?
I generally try to avoid buying the cheapest thing, but at the same time, while I always dream about owning the best, I usually end up with something run of the mill that works well enough for my need, gets the job done, and saves me a TON of money. I will then usually only spend money on something better and more expensive, when I've been given a darn good reason to. My shop is mostly Jet machines, grinder is a $110 Rikon...Jet works, works well, does the key important job, but doesn't add a lot of flare or extra features. The Rikon grinder is fine (I think it did require some leveling) and has been great with two CBN wheels. These things are nicer on my wallet.
Over time, I ended up with a Powermatic 3520C lathe. That was the result of having had two lathes fail on me, dealing with very, very lengthy tech support and RMA processes often spanning many months at a time, and finally getting fed up...then encountering an awesome sale for the Powermatic. That's usually how I'll end up with better, more expensive equipment...it literally becomes a need. The Powermatic was my fourth lathe in, heck, about two years? Most of the time though, I try to be softer on my wallet and buy good, functional, effective, reliable...but not "the best."
That pretty much sums up my approach.