I know it personal preference, but after working with X series for a couple of years now, and then loading 8.53. Ouch. Hard to look at and not as user friendly to move about as quickly as I like. Unlike your truck example, from 8.53 to now, I still click on X3, load a project. Arm a track and press record. When I finish, I hit the space bar and edit my track just like before except now... much easier to comp, adjust clip gain automation, edit quickly with integrated melodyne, press "I" and have a channel strip, zoom in/out several new ways, improved audio engine that allows for even core distribution, lower latency and very close to gap-less audio, drag and drop to change out soft synths, efx chains with user defined controls. A "mostly" better version of software. Not a 100% better but they had me at improved audio engine. The very core of the program. Hopefully they'll improve the automation more to your liking. I'm fine with how it is, but I'm not a power automation guy. Just mostly volume/pan.

I am going to go to X3 and Windows 7 and everything else next month so it's a moot point.  But for arguments sake, it has nothing to do with features or learning curve or "appearance" or anything else.  I am a gear junkie I buy literally EVERYthing, I love love love buying ****.  I love upgrading and new software and new features.  But what I really like is stability and being able to make music without crashing or glitching or buggging or getting the dreaded pops/clicks in your audio.  One user says that 8.3 was buggy for him.  For me, I happen to have come across a combination of software and OS that is completely bug-free so why would I switch?  (Answer: because I'm being forced to.)  You cannot say with 100% certainty that a certain software program with a certain OS and certain computer is going to be 100% stable, there's too many variables.  So once you find something that works, for me I guess it would take a ground-breaking development that I can't live without to switch.  Right now, my computer does everything I need it to do.  Anyway that's my argument for stubbornly refusing to be "progressive".

I think that's a logical approach Matt. Any software that can record and playback a glitch free reasonable amount of tracks is really all we need. I was a very happy camper years ago with a fostex 16 track reel to reel and a jl cooper smpte generator for virtual instruments, I was happy prior to that with a portastudio. :)  All these goodies we have now is really unbelievable icing. And the costs for today's studio equipment including software is also unbelievably cha eap in comparison. I used to spend SO MUCH MONEY! It's all in one's perspective. For me, I sometimes sit back and give thanks/shake my head, etc. for being able to create and produce with software/equipment that is so good it highlights me more than ever as the weakest link in my recording process. From Sonar 3 and up, I've always be able to at least mimic my tape days for pennies on the dollar. So I'm easy to please past that point.

"I used to spend SO MUCH MONEY!" 
 

That made me laugh! And for me is is actually at the heart of the issue.
The 70 and 80's
I was very pour working as a carpenter etc. But there was gigs in abundance so we played just about every weekend. Recording was something you did in a professional studio. The only affordable option was a stereo recording using a Cassette or if you were better off, a reel to reel. Later when the 4 track porta studios came along it didn't really help much. You had to figure out how to get 12 channels on to 4. So easier to just go straight to master. We just couldn't afford recording so it never happened. Last half of the 80's some of us had Atari's and MIDI was being pioneered. Note: there has been little improvement in using MIDI sequencing software since then! Really, very little. 
 
The 90's
I opened my music store which is a good move if your a gear head :)
but I was still poor! 
Now I could play with all the latest and greatest gear and at a low risk. Purchasing at wholesale, test driving and then selling before it becomes outdated. 
Multi tracking was growing in leaps and bounds during this decade. But 8 tracks whether it was reel to reel or digital (ADAT) still came in at over $2,000. For 16 or 24  tracks double and triple that. But more and more people were doing there own recording and small studios like I had were now affordable to the weekend bands and singer songwriters. 
Mastering was also up in the thousands if you bought a 1/2 track or then a DAT recorder. 
By the end of this decade you could sync your MIDI sequencer to your digital multi track recorder and computers could be used to control mixers, and now audio was possible.  
You still had to pay big bucks for MIDI sound modules, I bought a few which I still have. Look what you can get for free now! If anything I ever bought was a bad investment it will always be MIDI gear. Example= Korg 05W $1,400 now worth $10. Roland MT 32 $1,200 now free built into every PC sound card ( MS wavetable) 
 
The new Millennium: 
Even at wholesale by 2002 I had over $10,000 invested in a 12 track digital recording studio with MIDI capabilities. A lot of that equipment is still with me and it's duties have not changed much. Example the Yamaha 01v, my mikes and cables, NMS10's, Power amps etc. The only real change is the multi track recorder, MIDI sound sources and  the need for outboard processing.
From needing to spend over $10,000 to only about $1,000 for a PC and the software.  
But software is pretty boring stuff to a gear head, I still prefer to spend my money on my guitars and PA equipment upgrades. And I will upgrade my DAW next time round when my Window 7 64 bit computer dies. At that point I will look into Cubase because if I'm upgrading it will have to have audio editing. 
 
Note to Dave: All those little automation envelopes would not be needed if you have a wave editor. 

Cactus Music
"I used to spend SO MUCH MONEY!" 
 

That made me laugh! And for me is is actually at the heart of the issue.
The 70 and 80's
 

 
That sounds like a way too familiar story. It did seem like at a time that everything you wanted/needed was $1k and up. My 16track fostex retailed for around $7K. Bought an A&H mixer for about the same dollar amount. Money flowed from my pocket to someone else s all the time. It was a wait, save and purchase process. I remember buying my first digital reverb from yamaha that had a whopping 4 settings. Think I gave about $700 for that one. And that was late 80's early 90's money - oh and the big selling point was 12 bit operation. :) I imagine most of us at one time or another think about our plugs/vsti's in terms of black boxes. I know I do. I would neither have the cash or the space for those plugs if that were the case. It seems incredible at times at what I have access to now.
 
Talking about recording studios. I still have some 2 inch tape the studios charged me for safe keeping floating out there somewhere. :)