I've worked with multiple OS's as well, and they all have/had their issues.
My comment was primarily to discourage the "Windows = Unstable as a General Rule" statements, as things have changed considerably since say Windows 95.
Today, one may be a bit more stable than another in a particular situation, but it's not drastically (night and day comparisons of the past) in most cases. Exceptions would likely be found, but they're just that,
exceptions, not the general rule any longer.
It's also important to realize that a system is the hardware + software + OS, and a failure/issue can occur in one or more of those areas. Which can be mitigated, or even eliminated, by proper configuration (i.e. build a test system, and test the devil out of it). I realize you understand this aspect, but not everyone may look at it this way, which is why I mention this.
Unfortunately, not everyone has an IT staff, and if independent/SMB, haven't the funds, time, or skill to do it themselves. And given the various members here in MR, this aspect seems very important IMHO, as I've a strong impression most of our creative developers fall into the independent/SOHO/SMB classification rather than working for a Fortune 500 company that has deep pockets.
Small niggles that can drive you nutz for sure. But as you mention, bad updates, missed settings, or incomplete compatibility/stability testing can create such headaches.
I'm not saying it's perfect if these things are all caught, such as the application being used has strange behavior (= nothing the IT or user can do about it). But it's not what it once was (BSOD's left and right, even if the system was idle).
As it happens, I prefer to use Linux for servers (fan of RHEL myself for servers), and Windows on workstations (commonality makes some things a lot easier).
I see this a lot, even in other OS's, particularly with specific applications (poorly written).
In the case of creative suites, Photoshop is one IMHO (still does a lot of disk swapping).
As the CPUID's go up, they do tend to get closer regarding cost, particularly when you configure as closely as possible (memory capacity, HDD capacity, ...).
For me though, the support issue puts Dell in the lead instead. Additional hardware customization (3rd party or directly from the vendor) is a nice big cherry on top.
Software wise, I don't need OSX for anything, so it's doesn't hold much sway in regard to an existing software investment. What's left is stability and support, which Apple doesn't have any real advantage in the first category, and none in the latter
in my case.
This could easily work out another way for someone else, particularly if they do have an extensive investment in OSX based software. Not just the licensing costs where applicable, but training as well.
If they're available, sure. But it might not be when the system is needed, so I based the price comparisons off of MSRP.
But as mentioned, Dell and other vendors sell Refurbished systems as well, so for a fair comparison in that regard, you'd have to look solely at Refurbished units from any vendor you're interested in. Otherwise, it's not a fair comparison.
Not to say it's not relevant, as budgets are always important.
As per a Hackintosh, it's not advisable to use such a system professionally IMHO, due to any potential support issues on a system that has to earn it's keep (user/company makes it's income off of that machine).
For personal use, I say have at it for those that are interested. As per maintenance on them, it will depend on the hardware used (comes back to testing), so the results can vary wildly (from rock solid, to beyond flaky).
If there's a new model out, then overstock will be sold off as Refurbished. Otherwise, they're used machines they went through and fixed (some have slight cosmetic damage to prove it, as well as different S/N's).
I've the impression it's not the OS, but the applications (seen this sort of thing before; especially easy to see if you're comparing similar application suites <different vendors>, and test them on the same system).
Poorly written memory handling in an application is like shooting off both feet, and being expected to run a marathon.