For me personally, it is more of a
process of tool acquisition, than preference between the two choices you offered.
And there are degrees of each choice to be considered also…
For example, in 1974 I was a newly-married tire-buster kid working for a Goodyear store in Dayton, Ohio. I had gotten really good at selling tires and auto service while fixing flats, rotating tires, changing oil, etc. So one day the boss came to me and offered to make me the
next-guy-on-the list in the Dayton area to become a new mechanic. I would be given the next opening for a technician anywhere in the Dayton area. I was ecstatic, and immediately accepted. So the boss told me that the seasoned technicians at my store would now begin to officially train me on things like alignments, the “Sun Machine,” etc, etc. He told me that my training would take about 6 months, and that
I would be expected to buy at least one tool per week for my own tool box, so that by the time my training was done, I would have at least a bare minimum tool assortment of my own.
I was in hog heaven, and couldn’t WAIT for the Mac and Snap On trucks to arrive. I bought two or three items from each of them that week. With all the coaching I was suddenly receiving from my technician buddies in the store,
I was then more concerned with quality, than I was with quantity. However, fate was about to intervene…
Three days later, the technician in a one-man Goodyear service department in a nearby town suddenly quit his job, and walked out. My boss got a phone call from District Service Dept,
and that was it…I was a technician!!!!!
(Just so you understand, I had grown up helping my dad work on our antique cars, and I was a serious street racer each night in the area. So I knew how to do a certain amount of mechanical work. But my formal training simply didn’t happen. I had never yet done an alignment, fixed an A/C system, etc).
That night, my shocked wife and I drove to Sears, and maxed out our charge card
(I can’t remember if our limit was $500, or 1,000). 
I had a list from my buddy-technicians at my store, and bought brake and tune-up tools, suspension/steering tools, etc…plus an 8-drawer box.
So, on the OP’s subject,
at that time in my life,
I was definitely forced to choose quantity over quality. The only reason I bought stuff even as “
expensive” as Craftsman tools was because that was the only place I had that much credit!
(There WAS NO Harbor Freight back then, and the “cheap” tools which were available at that time were much worse, in my opinion.)
I soon found that I really needed more tools, and better tools, so I was an eager customer.
(The Mac and Snap-On drivers never forgot to visit me each week in those days!) Over the next year or so, I was trying to keep my credit in line, but still buying tools which I really needed, and still replacing “
good-enough” tools with better tools, which made a job easier and faster.
But after a few months of some very strong sales in my new service department, I was promoted again. This time I was moved to the position of Service Manager at our newest area store, at a shopping mall. Suddenly my job was more focused on sales and customer service. So I was no longer desperate to quickly fill out my tool collection with “
quantity,” since I didn’t often do the mechanical work myself. So then I began buying only Mac and Snap-On tools off the trucks, with an eye on building
a great arsenal of tools. Now I was more focused on quality than quantity.
About a year later, I got another opportunity. I took a test and was hired as an apprentice by the same AFL-CIO Sheet Metal Workers’ local that my dad worked for. This was about 1976 or 7, and I went from about $6 or $7 per hour to $14 per hour on my first day.
NICE! 
But now once again, I didn’t have the right tools. And I quickly learned that the apprentices who didn’t have tools
(and some bare minimum mechanical skills) got stuck with all the ****** jobs
(ripping out old insulation from dirty factory attics in boiling summer temperatures, etc, etc.) So I began again to start actively buying tools. At first I was concerned with filling my box with the bare essentials.
Thus I was again concerned mostly with quantity, not yet quality. I ended up buying many imported and second-rate tools, knowing full well that they were not good enough over the long haul. More importantly to this post…I was still working on my hot rods and classic cars at home, but could not afford the Snap-On and Mac tools I love for my home hobby box…especially while I still needed the sheet metal tools at work.
Now fast forward to today. I am self-employed, with a desk job. I still love to tinker with my Hupmobile, my 454 Chevelle, my 1958 Ford tractor, plus all the mowers and mechanical stuff at the shop, my home, and my kids’ homes. But “
tinker” is the right word. I don’t use my tools to make a living any more. And I
won’t do the really tough, really difficult, or really dirty jobs. So now I use my tools mostly to enjoy myself. And that includes collecting them.
(My apologies to those folks who hate "tool collectors and tool polishers". I don't wish to upset anyone.")
My dad was killed in a car wreck at 44 years of age back in 1978, and I inherited his small collection of high quality older tools…mostly Mac. He had always preached to me that they were something really special, to be treated well and taken care of. And I still have my
own tools which I bought new “
back in the day.” I have deep appreciation and respect for these superior quality USA-made tools. So for a very long time I have bought any bargain-priced Mac, Snap-On, Cornwell, or other premium tool which I happened upon at a yard sale. I would find a few pieces now and then, and just toss them in my tool box to add to my collection.
I thought I was the only one who gave a damn about these used premium tools, frankly.
But then I found
Garage Journal. And now I have the fever, and keep buying premium quality used automotive tools whenever I find them.
I have a pretty good collection of tools now, and don’t depend on them for a living.
So now, once and for all, I PREFER QUALITY OVER QUANTITY.
