Buying my first "real" bike. Need help making final decision!

I've been lurking this great community for awhile and I look forward to being able to contribute! As I mentioned, I am a newbie and have so much to learn about bikes/biking. I've learned so much just from reading everyone's posts. I've narrowed my first "real" bike purchase to 3 different bikes and I don't understand all of the specs completely. I've ridden all 3 and really like them all. All are within $50 of each other. All are 2014 models and I'd love any help on telling the difference between certain specs and also which one is the most "future proof." Quick background, I won't be commuting daily with the bike. I live in Chicago and it will be all urban riding with minimal hills. I'm 5'9, 180lbs. Thanks in advance! Here are the final contenders.

1. Cannondale Quick 4
Cannondale Quick 4 (b2) - Kozy's Chicago Bike Shops | Chicago Bike ...

Specs
Frame - Cannondale 6061-aluminum
Fork - Cannondale Quick carbon blades
Rims/Wheels - Element Xero C3
Hubs See Rims/Wheels
Spokes See Rims/Wheels
Tires - Kenda KwickTrax, 700 x 32c
Crankset - Shimano
Chainrings - 48/38/28
Front Derailleur - Shimano Altus
Rear Derailleur - Shimano Alivio
Rear Cogs - SunRace, 8-speed: 11-32
Shifters - Shimano
Handlebars - Cannondale C4
Tape/Grips - Cannondale Ergo Performance lock-on
Stem - Cannondale C4
Brake Levers - Cannondale C3
Brakes - Cannondale C4 mini linear-pull
Pedals - Quick composite platform
Saddle - Cannondale Quick Ergo Performance
Seatpost - Cannondale C4 aluminum

2. Cannondale Bad Boy 9
Cannondale Bad Boy 9 - Kozy's Chicago Bike Shops | Chicago Bike Sto...

Specs
Frame - Cannondale Bad Boy aluminum
Fork - Cannondale Fatty
Rims/Wheels - Cannondale C3
Hubs - Cannondale C4 Disc
Spokes - Black stainless-steel, 15g
Tires - WTB Freedom ThickSlick, 700 x 28c
Crankset - Shimano
Chainrings - 48/38/28
Front Derailleur - Shimano Altus
Rear Derailleur - Shimano Alivio
Rear Cogs - SunRace, 8-speed: 11-32
Shifters - Shimano
Handlebars - Cannondale C4
Tape/Grips - Cannondale Luxe Leather, lock-on
Stem - Cannondale C4
Brake Levers - Cannondale C4
Brakes - Cannondale Mechanical Disc
Pedals - Platform
Saddle - Cannondale Bad Boy Urban
Seatpost - Cannondale C4

3. Raleigh Misceo 2.0
Raleigh 2014 Misceo 2.0 Cross Bike

Frame - AL-6061 Custom Formed Butted Aluminum Tubes
Fork - 4130 Chromoly w/Disc Tabs
Shifters - Shimano ST-M310 Rapidfire Plus 8spd
Front Derailleur - Shimano Acera
Rear Derailleur - Shimano Acera
Brakes - Tektro Novela Mechanical Disc, 160mm Rotors
Brake - Levers Shimano ST-M310
Cranks - Shimano FC-M311 28/38/48t w/Chainguard
Cassette - Shimano 8spd (11-32t)
Bottom Bracket Sealed Cartridge Square Taper
Chain - KMC 8spd
Hubs - Joytech Alloy Disc QR 32h
Spokes - 14g Stainless Steel
Rims - Weinmann XC260 Double Wall
Tires - Kenda K-192 w/PRC Antipuncture and K-Shield 700x38c
Headset - Ahead 1-1/8 inch
Stem - Raleigh 100 Series Alloy Ahead 4-Bolt 7 degrees
Handlebars - Raleigh Alloy Riser 640/15mm, 31.8
Grips - Raleigh MTB Grip
Saddle - Raleigh 200 Series w/Satin Steel Rails
Seat Post - Raleigh 100 Series 27.2x400mm

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Permalink Reply by Frank Brichetto on February 7, 2015 at 7:07pm

Hey, Jeremy,

You're getting a lot of different comments from different folks, and face it, us bike rider types come in all kinds of flavors.

So here's my take on what's coming your way -

1- road vs hybrid vs fix gear - There is a place for every kind of bike - you're looking at hybrid types and that's a great type of bike. I've seen many, many happy riders complete rides up to a century on them. The heads up position is way better in commuting, IMHO, it's easier to see and be seen in traffic. The 700 x 28mm tires are generally tough, flat resistant, and offer better traction in bad conditions than narrower tires. They also roll easier and are measurably lighter than 26" knobbies.

new vs used - I have never regretted buying a new bike. EVER. I have regretted a few (OK, two) used bikes over the years, and ended up dumping them at a loss.

fixie vs gears - go gears. period. Kudos to Irvin for pointing this out. If you decide you want to master fix gear riding at some point, you'll want a totally different bike, wheels, set up, etc. and then go do that.

When you want to go to a drop bar road bike, get one. There is nothing wrong and everything right with having multiple bikes at your fingertips.

road - recreational - commuting riding styles - The great advice, attributed variously to Merckx, Coppi, Anquetil, and others holds true - "Ride the bike, ride the bike, ride the bike." So - get that Bad Boy, you know it's already calling you by name. Ride it, enjoy every mile, and have fun.

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Permalink Reply by mark stetson on February 8, 2015 at 5:48pm

I can't disagree with anything Frank said above, even the part about new vs. used regrets. That said, I think that if you shop carefully, you can find a comparable bike used and save money.

Since it's been mentioned already, I'll add that I don't find flat bars very comfortable for rides of any distance - they make my wrists hurt. I'm old, you probably are not - but that's the sort of thing you won't figure out until you have some miles on whatever you purchase.

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Permalink Reply by Jeremy on February 9, 2015 at 4:21am

@Frank

*SLOW CLAP*

I felt like fireworks should have let off after I got done reading your last post. The Bad Boy did indeed call me by name. Thanks for the feedback. This has been a great resource for me and I am excited to be a member of these forums. Now let's all mount up with Frank's inspiring words echoing in our ears and ride, RIDE because we are free, RIDE because it is our right, RIDE because the roads and trails call us. Do not ride gently into that good night my friends!

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Permalink Reply by Tom A.K. on February 9, 2015 at 5:03am

+ 1 Jeremy(Rudy). It's great to hear from a happy new Chainlinker ! Ride on !

Jeremy said:

*SLOW CLAP*

This has been a great resource for me and I am excited to be a member of these forums. Now let's all mount up with Frank's inspiring words echoing in our ears and ride, RIDE because we are free, RIDE because it is our right, RIDE because the roads and trails call us. Do not ride gently into that good night my friends!