I think we are more in agreement than disagreement Kevin. 
I try to educate people on these things as generalizations can also be wasteful and lose you a deal on some things. Any cutting tool has to be looked at in terms of "useful life", absolutely.
I'm just not in the "new shiny = Good/better' crowd. (Not implying you are...) Nothing wrong with new shiny, but that's not always a deal, and I'm all about deals at this point. Hell I could probably stop buying tools today for most of my remaining years and not "use up" what I have now, but where is the fun in that?
Some of what I buy I don't have and may never need, some is an upgrade to what I have, and some is for friends or resale...
Sometimes there is gold under a layer of rust. Sometimes it's fools gold also though, so you need to educate yourself before buying or know that it's sometimes a risk when you do buy something. Is the cost worth the risk?
That answer is always "it depends" (Again using the "you" as in general terms and aimed at me as well, not specifically at you Kevin)
I agree with you 110%. And I am not taking anything you say as an attack or implication. When it comes to machining, there are so many things to look for when it comes to the deals. I'm not a "shiny & new" person either, but like you, I want to take care of what I have and keep things in good shape. Myself, I have tools that I made, or tools I purchased years back that looks like they have seen the better days, but are in fact close to new, but age and the weather has taken it's toll on a few things. If a person is not familiar what to look for as far as the sharpness of perishable tooling though, it's sometimes safer to buy new. The main reason that I buy new sometimes is that I learn to become familiar with the tooling. Whether it be an endmill a tap, or even a set of Mics, you know where the tool has been and what it's done in it's time. And with more and more people becoming "home machinist" I have saw a lot of stuff on CL, and flea markets or garage sales, that have a ridiculous price on them. I know what the tool or tooling is, and what it's worth, but others that just bought that lathe or mill and want to become home machinist, may not have a clue and will buy junk or spend three times what the item itself cost new. It's a shame that people want to take advantage of people like that for a few dollars.
I try to educate people that are just now becoming those home machinist, and at times, I don't convey things real well in typing out on the computer, as to what's actually going through my mind, and it does rub some people the wrong way (not saying that you do, so please don't take it that way) I'm just trying to help them out with what I have learned over the year, and from my experiences with what I have run up against.
And like you, when it comes to buying, I'm all for the bargains. I'm not rich, and when it comes to having anything to do with machining, whether it be precision tools and perishable tooling, it can get to be expensive really fast. I think a lot of sellers compare Machinist to the price of gold. I missed out on some good deals a number of times. One that will always stick in my mind was when my mom and sister went to a garage sale. My mom called me later and told me that a guy down the road had some "C" clamps with numbers on them, and some other odd looking tools. He also had a nice toolbox but he painted his name on it and he only wanted $25.00 for the toolbox and $10 for the "C" clamps. Seeing that it was right down the road and I knew almost everyone alont there, I asked her what his name was, that was on the toolbox. In my head, I am envisioning a ****** toolbox with bright neon orange stencils with his name. She said his last name was Kennedy. I couldn't get down there fast enough. Sure enough, there was an 8 drawer Kennedy tp and the two drawer middle base. $25.00. The "C" clamps.......0-12 Mitutoyo mics. Already sold, and the toolbox was the only thing left
He was a Toolmaker, got pissed and quit his job and was selling everything.
Yep...I'm all for those bargains
At least there is a number of people on this site that tries to help others though, and that's what it's all about. I don't know it all and never will, but what I have learned from my experiences as a tool designer and as a toolmaker, I will try to pass on to others that may not know. To me, there is nothing any more satisfying than getting in front of a mill or lathe and start turning some handles. In just a few minutes, you get in the "zone" and the problems of the day go away. Total relaxation, or it is at least to me.
So yes, you and I are in total agreement on things, just in different words
