Too Afraid To Upgrade!

Question

So what's the deal with all of these Apple commercials about how, +"it just works,"+ when I read endless posts about how Leopard seems to be bottoming out a whole bunch of savvy Mac users with the latest hardware to boot (pun intended)?
I mean the poor Vista guy getting castigated by the pretty OS guru while Mr. Leopard (Drew Barrymore's boyfriend) there is just cruising along with no mention about all of the incompatibilities and other issues that seem to be plaguing Mac user after Mac user after running the upgrade, is just the latest disavowal by the Apple marketing people of some real problems that are going on with this latest release.
Don't get me wrong, I'm all for creative marketing campaigns and Apple has some of the best, starting with the 1984 Orwellian commercial that started the whole phenomenon. But after reading post after post about how Leopard is causing all kinds of problems -- especially with users who have similar hardware as mine -- I'm left with a sense of being: Too Afraid To Upgrade.
I purchased a retail copy of Leopard just after it came out in Nov. of '07, and was expecting to throw on the upgrade like I've done in the past (both client and server versions) and watch it do its thing and get rolling with a new and improved "hot" OS on my bad a*s MacBook Pro. And like a diligent former UNIX Sys Admin and a former member of the Apple Consultants Network, I did a lot of reading up first before the upgrade was to commence and that's what stopped me "butt cold."
I mean when you're reading things like the user accounts no longer have administrative permissions after the upgrade, or the built-in Airport stops working with 802.11g wireless networks, or all kinds of software including Parallels (which is what I've got running on my system) tank or stop functioning, and let's not forget peripherals stop working after the we come up to Leopard, that's just freaks me out.
Also, all of the extraneous ways proposed by very learned users on how to upgrade that involve the old archive and install, clean install, or even the more radical target disk install, seem to me to *totally defeat* the "it just works" slogan and years of simple and easy upgrades that I've been doing since System 7.6! Even going from 9.2.2 to OS X was a snap on my old G4 500MHz AGP Sawtooth. Actually, I've thrown a number of upgrades and wacky configurations on that system including bumping it up to OS X Panther Server which runs just fine (except for the known USB 2.0 upgrade card/sleep issue that is intermittent and I've learned to live with).
So why is Leopard totally "off the rails" here? And more importantly for me, what the h*ll do I do now?
I really don't want to go the archive and install route because that would entail reinstalling a ton of my software (fully licensed), and trying to get Windows XP/Parallels back on there and hope the Microsoft activation protection doesn't kill my reinstall. Also, I really don't have the darn time to spend a whole weekend trying to get both mine and my wife's user accounts back to the same state as they were with Tiger before the upgrade. Sure backing up is fine with me and I'm hoping that Apple's backup software will do the trick, but going the +"whole nine yards"+ with the thing seems a little too excessive for me; I'm not that 30 year old Mac guru I used to be, I'm in my forties now and I just want the thing to work, you know? Which is why I'm all about Apple and the Mac to begin with.
So are there any success stories out there? Or is Justin Long and Steve Jobs pulling my leg?
My other question is, if I go "commando" and say "forget it" and just slap on that upgrade, and then attempt to pump it up from 10.5.0 (which is the retail DVD that I got, like most people) to 10.5.2, am I just fooling myself into thinking that all will be well and when the computer restarts I won't get the evil WINDOWS Blue Screen Of Death?
What should I do? Just wait for 10.5.3? or, wait for OS X Lion (if that's what they're going to call it)? Should I just use the DVD of 10.5.0 for a coaster? Should I let the geniuses at the Apple Store handle this one for me at a cost that I shouldn't have to pay over and above buying the software? I've been in the Mac game for many years and always come to this discussion board first when I need answers and I usually find them (and have given a few of my own); however, this time I'm at a total loss and am +stopped dead in my tracks+ before I've even begun.
_You all scared me!_
I need some reassurance that upgrading to Leopard is worth it and that I can do it without having to rebuild my whole system.
As Pink Floyd once said, "is there anybody out there?"
Thanks a bunch,
Nick from Boston

Answer 1

Nick, I see you're running OS X 10.4.11. Working OK for you I assume? Try going back at least a year in the forum posts and you will see the very same posts about the very same problems in the version of OS X you are running now. Go back farther and you will the very same posts about the very same issues for EVERY version of OS X that was ever released. Some people have issues with anything they attempt to do and they post here about it for help. Think about it for a second. If Leopard were really "off the rails" you wouldn't be able to login to this forum because it would be overloaded.
Apple's commercials are indeed correct. Macs "just work" for 99% of users. You know all the voodoo people post abut here? Repair permissions, don't do an upgrade, do an archive/install instead, do this, don't do that? Most of it is pure baloney. My Mac shipped with OS X 10.3.6 in 2004 and I have applied every single update, every patch, every security update since then. I installed OS X 10.4 Tiger right over the top of 10.3 with no issues what-so-ever and have applied all patched and updates since then. This past weekend I installed OS X 10.5 right over the top of 10.3 and 10.4. Then I applied ALL of the updates since then in one massive Software Update session. I came up on a fully patched Leopard installation without ANY issues. I can even type upper case letters in Google Mail (which some people claim was broken by the latest security update. It wasn't).
Luck? Not hardly. Those of us who seem never to have many problems or issues have several things in common. We know precisely what we have installed on our systems at all times. We tend to stay away from most of the little add-on "thingies" that are supposed to enhance OS X because we know they almost always break when a new update comes out. And most importantly we do our homework before applying any update. We check to make sure our hardware and software is in absolutely perfect condition. We make backups. We check with third party developers.
Yes, if you took to heart all the wailing and gnashing of teeth around here you'd be afraid to update anything. Most of the heartache is self-inflicted however. Know what you have going on before you upgrade and you will not have a problem. Trust those who know.