I still think going AG is worth it, but I'm thinking one should not expect a usable batch the first 1 or 2 brews...
While IMO most of your post was accurate, I totally disagree here. My first AG weekend was a clover honey nut brown ale and a homemade farmhouse ale recipe (attempt at WI New Glarus "Spotted Cow"). Both 10g batches turned out to be absolutely amazing. Now I have 4 Cornies full of AG premium homebrew at $0.15 per 12 oz.
In my opinion, the key is
DO YOUR HOMEWORK before attempting an AG brew day. You are sitting upon a wealth of knowledge here at HBT. Take advantage of other's experience. Check out Yuri's AG videos(don't feel intimidated by his technical jargin the first time around

/poke) as well as the numerous other HBT/youtube AG videos. I personally spent over two months of daily forum-browsing research before I started chipping away at my desired equipment and brewday routine.
Look for good deals on equipment
over time, don't just sit down and buy everything at once. I suspect most of the guys around here pieced their rigs together over the length of their brewing careers as they stumbled across deals. I personally love DIY projects, and was able to save some serious $$ by making all of my own equipment from scratch. Check out the How-To project threads. Keep an eye on
www.morebeer.com for their Deal of the Day. If you're lucky like me you'll snag a $230 15gal SS brewpot for $100 (free shipping).
As long as you do a mental run-through of the brew schedule and make sure you have the necessary equipment cleaned and ready - you should be fine. The depth and multi-layered flavors created from mixing your own malts is VERY rewarding and worth the effort. All in all going AG was extremely exciting for me, friends and family were a little overwhelmed by my nonstop talking about the upcoming brewday. The feeling of accomplishment is easily 100 fold over extract brewing for me.
Like I said, do your research. If you get the AG bug... you'll know. It will start to consume you like it has most of the AG brewers around. Brewing is one of those hobbies that can be as complex or as simple as you make it. Do what feels right and Don't be afraid to try new things!! That's what this is all about
I hope this helps. Cheers!