I'll start this with saying I don't know your specific circumstances, so I'm going to make an assumption and forgive me if I'm wrong.
I have worked with thousands of mechanics through my jobs. (maintenance manager for some extremely large operations) I absolutely advocate buying the right tool for the job, buying it once, and having it for the rest of your life.
With that said, make sure the tool you are buying NEEDS to be one of the uber-expensive brands to fit that bill, and make sure you are going to use it enough to justify it. I've seen a lot of apprentices roll in with $20,000 worth of cabinets and basic S-O tools, spend their first years pay (via credit) on more S-O stuff than they'll ever need, and pay the price for many many years follow. All the while the journeyman mechanics are there with their well used (and well cared for) rigs with 1/4 of that in tools, spread out over 20 years of work... and doing a better job with much less invested.
The point? Be selective. Pick away at it. Don't buy a snap on hood ornament adjuster for a 54 rolls royce for $300 when you know you'll only use it once. It may be a great conversation piece in your cabinet, but weigh it against things like accumulating debt, buying a house, etc.
As far as buying tools go (the original question), I would look at the ease and availability to get replacements as a high priority. S-O does well for that, I don't know how MATCO compares in your area. My personal philosophy (as a part-time mechanic at best) is that I only buy the high $$$ tools when it's 1) complex, or 2) used a ton. As a result, my ratchets, sockets and wrenches are the only things I splurged for S-O on. The rest, is guaranteed for life stuff, by a local big box store. I can get replacements easily, and generally they put up with my usage levels.