Most of the people that take their car in don't even know enough about tools to make a judgement. I don't ever remember going into a shop and thinking "oh man these guys are hacks look at those Canadian Tire boxes" or "they remortgaged their house to buy all Snap-On tools, they must be really smart mechanics (and really dumb/single, financially unstable guys)"
Most people don't think that way. Maybe the hand full that know wrenching will recognize your financial effort you put into your tools, and even then that means nothing about your skills.
All this being said, I do buy SO, Mac, Proto etc. I also am very minimalist compared to most people on here. My box is a Mac MB1004, not stuffed to the brim and I only keep what I need. I don't need 25 ratchets, and a million screwdrivers. For the longest time I only ever had my ratcheting stubby screwdriver. It's worked for 99% of the situations in my 5 years working on helicopters, and now my transition to heavy duty/industrial I still find it sufficient.
I genuinely feel for you automotive guys, getting caught up "needing" to buy SO much stuff and having condominium style tool boxes to store it, all while being stressed under time and potentially not even making money with flat rate sometimes. We all appreciate nice boxes and tools and a good looking setup, but being a mechanic is not a **** swinging contest about who has spent the most money on tools. The customer and surprisingly lots of employers (maybe not so much automotive) don't care that you pay the Snap-On truck $200 a week to "be the best".
Just my $0.02, seems a lot of industrial/equipment type guys think similar.
Any who here's my box.