It's hard to say as I wasn't there, other than the $200 fitting I could see this either way - the guy may have been a total ass, or he may have not been that bad depending on his attitude, tone, pushiness, etc. To answer your question, you *certainly* don't *need* a $200 fitting. You're certainly correct that it's absolutely important to buy a bike that's the right size, but even if you pay for the fitting (which I recommend, as I prefer not to risk having the guy try to tell me my size is the same size as whatever they have in stock) it should be like $35 for a basic fitting that tells you what size bike you need and is credited back to your purchase if you buy a bike there, no matter what the bike costs.
Back in the day, it used to be that the frames were the same and the components just went up as you payed more. Nowadays it's kinda the opposite - you don't get much by upgrading your components (unless they're really crappy) but as you get more expensive the frames get better and better, especially in carbon fiber bikes. It's also REALLY expensive (at least without technical expertise and the ability to do it yourself) to upgrade components later - I asked about upgrading my Sora shifters to Tiagra. The bike shop said it was $250 retail for the shifters, so even if they gave me a good deal it would still be $250 including installation. And that was just the shifters, not the cables, derailler, chainring, etc. Also, Sora and Tiagra are 9 speed, while 105 and up is 10 speed, so if you want to upgrade from one group to another you have to replace everything all at once.
I definitely agree with you - I wouldn't buy anything less than Sora on a road bike. Sora is pretty solid except that the shifters annoyingly only let you shift from the hoods. Tiagra has the double levers on the brakes so you can shift from the drops, and it's a pretty solid set. 105 is ten speed and billed as "entry level racing" - most people cannot tell the difference between 105 and anything above it.
You said that up to this point you've just ridden a Walmart special mountain bike. You also mention the CAAD9. In road bikes, there's 2 general groups - race road bikes, and "endurance" road bikes. If your big ambition is to go fast and feel like you're going fast, or to race your serious road bike friends, a race bike is probably what you want. But a race bike puts you in more of that leaned over position - it takes a while to build up back muscles to support yourself, and it's way more important to get a good fit to be comfortable while riding. It's also harder to enjoy the scenery, look for oncoming traffic, or just chat with your friends. The bike is super responsive, but it takes a certain amount of concentration at all times just to keep in going straight. A CAAD 9 is in this group.
On the other hand, you have the "endurance" road bikes. They're nearly as fast, but they're a lot more comfortable and easy going. As for speed, the difference in speed between a mountain bike with knobby tires and any decent road bike is like 30%-50%. The difference in speed between a race road bike and an endurance road bike is like 3%, and 2% of that could be eliminated if you adjusted the setup to resemble a race road bike. So not a big deal. But it's a lot easier to get an endurance road bike fitted right (there's something I've found about having the handlebars above the seat that makes getting a comfy fit soooooo much easier). It's way less work to go straight so you can totally just enjoy the scenery. And it's easier to talk to friends you're biking with or to look over your should or down a street you're coming up on because you're not all hunched over.
Don't get me wrong, when I want to hit it hard and go fast my race road bike is great. But I actually bought a 2nd "endurance" style bike because sometimes I just like to peacefully cruise around and I could never comfortably do that on the race road bike (it's comfortable while going fast, but never quite comfortable going slow for some reason).
You're the one to decide, but it sounds to me like a endurance road bike would be what you're looking for. I bought a Specialized Sequoia (the Allez is their lower end race version) -
http://www.specialized.com/us/en/bc/...=39270&eid=117
It's $880 full retail, so it's around your price range (I know my local bike shop has it on sale for $760). I rather like it, my only complaint is that it doesn't have more clearance for bigger tires (or fenders) - I don't think it would take above a 28c tire. But it does have fender and rack mounts. It has Sora components (with a Tiagra rear derailler). I also bought it because I needed something I would be comfortable leaving locked up, and this was the lowest I was willing to go for a road bike. I find not being able to shift from the drops a little annoying, but I'm considering buying a Tiagra right shifter off ebay for $50 then paying the bike shop another $50 to install it. A lot of people just ride on the hoods anyways, so you might not even care. I've found the Sequoia to be a real decent ride, though it's certainly not the absolute smoothness of my full carbon frame.
Just to contradict myself, it appears that the Sequoia uses the same frame for the higher and lower end bikes. If not being able to shift from the drops doesn't bother you, I might suggest buying the lower end Sequoia, then if you really get into road biking saving up and buying a much more expensive bike that comes with a full carbon frame like an entry level Specialized Roubaix.
I know the other manufacturers sell their own "endurance" road bikes, I'm just not as familiar with what they're called - anyone who knows please feel free to comment.