When I was younger, with all of the pressures of life and family, I bought based on developing capability in the shop. Functionality for the money was the focus with regard for the type of work I was doing and for what I wanted to do. On occasion, primarily birthdays, Christmases, and when an unexpected small windfall made my way, I would splurge a little to buy a little something extra. Later on, when the income looked a little better, I started buying more that came my way due to opportunity, and added to the shop capability, and didn’t necessarily reflect an immediate need. As the children reached adulthood and many of the regular debts were finally paid off, I started buying based opportunity and what I liked and saw value in. Need was usually secondary or nonexistent since by then I already had most of the capability needed for most of the projects I would ever feel inclined to undertake. It really became a bit of a obsession in that it is difficult for me to pass up a good used traditional tool at a bargain price, even though I may already have several. I do enjoy the process of taking an old tool and restoring it to a useable condition. The result is that I have entirely too many of some things, more that anyone could possibly ever use. Having said that, I have started letting a few things go to other users.
Through the years a few low level collectables and some higher level newer used tools have found their way into the shop. My experience with them is that the performance between the high end newer tools and better quality used tools is pretty much negligible after the older tool is tuned. So placing functionality above resale value and prestige , I have purchased a relatively (compared to the total volume of tools) few new traditional tools unless older tools were unavailable to me or the new tool represented a tremendous bargain of performance compared to price. I will admit, however that I have given in to “bright and shiny” in my later years on occasion, but I have often regretted it afterwards.
Being retired has afforded me the time to hit estate sales, yard sales and similar occasions to pick up additional goodies for the shop and the time to spend putting them into working order. There are always pressures that direct what you do and my life is no different. What makes a tool “worth it” it strictly up to the individual.
Whatever you do, have fun.