OP works for a tech company. As such, showing up with a Nixon-era Cessna is not going to earn him anywhere NEAR as many cool kid points as showing up with one of the Rutan numbers like a Long-EZ, or something he can pretend that he built himself like an RV. ("I 3D printed it, lulz")
I say that being a total Beechcraft nut and having disdain for any airplane who refers to its parked mode as "grazing". None of my tech coworkers are impressed with my airplanes. They are impressed with my ipad and its aviation apps. Xavion was a big hit before the owner went full retard with the pricing model. Nerds like math, and aviation is a giant calculus problem. Work that angle. If they perceive that you fly the equivalent of a 67 Chevy Nova, the conversation is gonna turn sour.
I did the commute thing for a few years, and am about to restart it. The 100% bonus idea is amusing, but probably not reality -- especially if you just poured our a half day's worth of brain juice to do an IFR TEC route in the Bay. That said, you *will* be in a very good mood all day, because you started it by doing something awesome. After slaying the "I cheated death" dragon first thing every morning, code problems seem trivial by comparison, and THAT attitude is what will have follow-on benefits.
I'd get the license at a local flying club, and start doing the "best airplane for me" game. My first one took me a year or two to iron out, and I still got the answer wrong. If you are remotely analytical, this game is going to be HELL for you. Aviation is an emotional game, not a logical one.
Have fun with it. That's the whole idea, right? Even if you spend *more* time flying than driving (and I did in the LAX area when IFR) -- you did something 99% of the others would wet themselves even considering. The benefits aren't really tangible, but they ARE real.
$0.02
- Mike