"Do I buy a new bike? Do I upgrade my existing ride? Should I trade in my current ride or keep it and buy a new one? Will I continue to ride as much as I really would like?"
Alright. That was more than one question but I was just on a role and they are all related. I have an old road bike from the early 1970's and I have a hybrid/cross-over bike from the early 2000's.
Here is my Cannondale:

Pros:
- Slightly larger tires so I can go off road if necessary
- Quick enough on the street
- small shocks on front fork and on seat post - no overkill, just enough help
- sturdy frame
Cons:
- Slightly too large of a frame for me
- Heavy compared to a road bike
Here is my Gitane:

Pros:
- Light! Even for a 35 year old bike it is really light.
- Skinny road tires
- Upgraded Shimano rear derailer
- Cool ole vintage ride!
Cons:
- Tires might be too skinny for the incredibly smooth roads of OKC
- Slightly too tall of a frame for me, but I'm actually getting used to it
- 10 speed, which is actually okay. Because I never use the highest or lowest gears.
- Needs new brakes
- I'm wondering if I am putting too much torque and wear on the old welds and joints
Yes, I'm keeping the stock kickstand on the old Gitane. It is just too stinkin' handy! I can park it in my office and not have a scuff mark from me leaning it against the wall.
What are some of my requirements for city riding?
- Light
- Not many gears are required; I usually hit too many stoplights, intersections, etc..
- I can sacrafice the toughest frame, a light steel frame will take care of me.
- Some slighly larger tires than road bike tires. I've been alright with road tires but I'm finding that I might be getting more and more flats cruising around the city. I'm jumping curbs, going up and down grassy hills, and hitting the occasional pot-hole.
I always compare Specialized to Cannondale because the same shop usually carries both. I can't find if Cannondale owns Specialized or the opposite but I'm sure I can ask the local shop and they will tell me. But when I compare two equivalent bikes, one Cannondale and one Specialized, the Specialized always "feels" lighter. I guess I'm partial.
Here is the Specialized Tricross:

This is the kind of bike that immediately pops into my head when I spill out my requirements. It has the road bike geometry, handlebar and lightness but still has the slighly larger tires. The picture I showed is the triple gear front crank (I appologtize for my lack of bike terminology) but I would be happy with just the double. But both show as the same price on the website. Weird.
Another interesting ride, Specialized Sirrus:

This bike is about $700 cheaper ($1,300 compared to $590). It still has the lighter frame, slightly larger tires and a handlebar like a mountain bike for improved control. This looks like a great starter bike for city riding.
But wait... oh crap! This looks like my Cannondale! Ah poo! I wanted to go buy a new bike. Maybe I just have new bike fever. Maybe I don't need to upgrade. I just need some new pedals and a better saddle and I'd ride my Cannondale more often. I can deal with the weight for a while until I decide I really need to upgrade.
So, I have my city bike now I guess. Darn! I wanted to go shopping! I guess whenever I can actually find the time to get out of the city and go on some longer road trails I'll find reason to buy a decent road bike.
Cheers,
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