More on Why the Bike & Grr the Bike

Alright. I laid out some basics, and am going to skip straight ahead to the shop talk,
as that's essentially what happened for me in buying the bike.

Tri bikes, when one gets serious, are alien spaceships.

I was glad to know I had no interest in one of those, from either a practical stand point - I'm not good enough for it to make sense; a financial stand point - $4500+ anyone?; or an aesthetic standpoint - the high forms of any niche are an acquired taste.
I knew a couple of things: I would pry use it for commuting a fair bit, and therefore wanted something that was almost shitty enough that I wouldn't mind locking up. This isn't the last bike I'll buy, so it didn't need to be top of the line for my price point, but should be an educational bridge from single/fixie world to road-land. I did not want a ladies bike, as they all seemed to have condescending paint schemes.

The original plan, owing to my budget, was to have Charles Spano, friend and son of a custom frame builder, help me ebay a great bike. For around $500. I want to be clear that this would have been totally possible, had I more persistence, time, and trust that everything would ultimately be okay. Even my coaches were alright with this plan.
In order to shop at distance, I needed to make sure I knew my frame height correctly, so I went down to Cynergy Cycles in Santa Monica to get a rough fit, and ride some Specializeds.

Long story short: I ride an Allez, which is the bottom of the good line of basic road bikes. It LOOKS H.O.T.

I want this bike. I want it. It costs $880.
That is $380 more than I had planned to spend.
I ride it. It rides well, but is a strange transition from my old Surly, which I think was too big for me, caused me to over-extend my upper body to the handle bars, but which I got used to, and I am still un-learning.
They urge me to ride the women's version of the same model, which looks like:

This is not a cool bike. It is almost pastel, and it has floral decals. The handle bar tape is THICK. This is rude.
I ride it, but I don't really pay attention to it, because I just can't make myself. This bike is $940. Hmph.

A week goes by, where I stress over whether I will be ROYALLY SCREWING myself by not getting a women's frame (mental freakout/hyperbole) and how dumb I am being to let aesthetics trump performance (mental abuse/hyperbole), and the feeling that if I'm dropping that much dough, I should get what I damn well want (clarity/sanity).
One day, driving on a random street, I go, You know what? Screw it. It's MY damn bike, lots of ladies rode man bikes for long enough, I'll be FINE, and then when I eventually get a ladies bike, I'll know whereof the differences lie.

I go back to Cynergy.
I ride the Allez again, and crazy Randall the world's ultimate salesman soothes my fear that I should be buying a women's, and says its okay to get the Allez. It's a nice bike. I say to Randall, just to be educated about this, let me ride the Dolce (women's frame) one more time. Except they don't have the Dolce I rode last time in my size. Now all they have is a Dolce Compact. This bike has nicer gears than the Allez or the first women's bike I rode. This is dangerous. This bike costs $1600.
I ride it, for about 5 minutes.
I didn't cry, but I could have.
It was a massively better bike, and you could feel it from the first moments. This is a machine I am going to be on for hours at a time, covering 100's of miles. I have no money, but I want to do this for myself. I want to go to the outer limit of what I am comfortable with financially, and get a bike that will make me love this race.
I buy it.
I go into overdraft, unwittingly (I thought I had $3000!) at that moment.

Possibly more troublesome, it looks like this:

Puke. Really. Puke.
Apparently the CEO of Specialized had been at the store 30 minutes before I came in to ride. That was my chance to let someone know. Instead, I'll probably just paint the frame. What's another $100-300 at this point, right?

I'm in deep.