My local Craigslist is like the wild west of used bike sales and I have a hard time justifying spending $125 on a 10 year old Trek bike with rusty cabling and fossilized brake pads. I'm looking to replace my daily beater/rain/winter bike which is currently a really run-down Walmart mountain bike bike various Nashbar/entry level Shimano replacement components that's never quite shifted right through all of the gears. Even after it was gone over by my LBS they didn't have much luck getting the existing derailleurs to play well with the frame.

Assuming REI has another 20% off coupon sometime in the near future that's valid on bikes I was thinking of picking up one of these:

Diamondback Wildwood Citi Bike - 2010 Closeout $199.93

I'm not interested in spending more money on this bike. This is the one that's going to get locked up outside, ridden around in the rain, in the snow and will bear the brunt of any bad weather.

The positives I see are:
26" wheels: can transfer my existing Schwalbe Marathon Plus & Schwalbe Marathon Winter tires
21 speed drivetrain: cheap cassette/chain replacements
full sets of eyelets and mounts to transfer my existing rack & full fenders

The negatives I see are:
suspension fork & seatpost add weight and unnecessary complexity
riser handlebar increases wind resistance and limits bar-end mirror usage
bike geometry likely limits use of my current Nashbar Glide saddle

However, assuming I could get a size 17 for 20% off I can't see it being all that bad of a deal for $160 + tax.

The only problem I see with your plan is that the 20% off coupons at REI are on regularly priced items, not sale items. It would be nice though if you could.

7 speed is fine, promax v-brakes work just fine. I'm sure the shifters are just fine.

Wheels will most likely suck pretty badly. Just a warning. That's typical of entry-level bikes though.

Keep looking on CL. You have a while before winter starts and you can probably find something thats used, a lot nicer, and is more your style than this. What if something like a wheel goes out on this cheap-o bike? Would it be worth the hassle to replace it? Might as well find something that is quality on CL that you can keep for a while and repair as you go.

Have you gone and looked at any of these CL bikes? Maybe you have, but this is the time to buy bikes as people are not that excited to be riding them in the winter so there isn't as good of a market for them. You might need more patience. Even in the tougher markets there can be great used deals. That Diamondback isn't bad, but I suspect its going to be pretty heavy if that matters to you.

I think my current bike weighs in just short of 30 pounds so weight won't be much of an issue. I'm still browsing Craigslist but there's a lot of chaff to sort through. For every bike worth seeing there's at least 10 more "just tuned, need nothing, ignore the rust on the cables" ads for 15 year old bikes that don't shift much better than my existing bike. I've already replaced the front wheel on this existing bike 3 times due to cracked rims (and I do not ride off curbs with this bike) so I'm certainly willing to throw money at any replacement bike as parts wear out.

Any 15 year old or so Trek 800 series mountain bike or a simular brand (Giant Diamondback Gary Fisher etc.) will shift better than your current bike. Just because its 10+ years old doesn't mean its a bad bike. Do you do work on you bike or just take it to the LBS?

There's not much at all separating that Diamondback from a Walmart bike. The components look similar. The frame isn't especially good. REI will likely have more competent people assembling the bike, and their customer service is good. Otherwise, I'd pass.

A 10 year old Trek with rusty cables and fossilized brake pads, on the other hand, will generally have a good frame and might have decent components. Cables and brake pads are cheap and need to be replaced regularly anyway. I got an '89 Specialize Rockhopper on CL for $120 that was in mint condition. I replaced the tires (only because they were knobby), installed a rack and it was ready to go.

CL takes patience and a good eye, but it's the only place you'll find what you're looking for (assuming you're looking for a good bike for under $200).

There is a reason they call entry level big box bikes BSO's. I worked on a friends' kid's bikes. I swapped out the twist shifters for friction shifters and I still couldn't get either one of them to shift decently.

I ride my Xtracycle year round. It may take a little more maintenance, but, I would rather ride a decent bike I like and trust, all year round, than a BSO half the year.

What does BSO stand for. I'm guessing but can't quite figure it out.

https://tinyurl.com/35uwtnb

Never thought of that. I should keep my minid out of the gutter and on the street.

Go to Simple Living Cycles in Framingham, MA (website:https://www.slcycle.com/752.html). Pick up a Mongoose Kaldi (https://www.mongoose.com/usa/eng/mtn/...=2633&enc=mtn|). You'll have a brand new bike at a reasonable price.

Winter makes Drum brakes and IG hubs an even better thing,
add a chaincase and all you have to cope with is the weather..

Winter beater? Find a fully rigid mountain bike on CL.

I picked up this year's winter beater for $50. Picked up last years for $20.

Those look like some really good prices on a number of bikes. If the OP is tired of looking for a used bargain and is willing to pay $200 I think this place would be the way to go assuming they haven't sold all those bikes. Some of those deals seem really good. It wouldn't be a beater though. LOL

Check out Coops, LBS that sell used, garage sales, auctions, and craigslist. I am currently looking over an old Mountain Bike I have sitting in my mothers basement.

Actually I've been meaning to make a trip out to Simply Living but the hours are impossible for me during the week. Due to the high concentration of students here in Boston there are no ridable $20 used bikes on Craigslist. If you find someone absolutely desperate to sell/it's stolen you can find something for $50-75 but the entry point for the majority of bike brands is $100+. I'm still keeping an eye out on Craigslist.

Just for the record the current bike has a Shimano Acera rear, Alivio front, SRAM MRX Comp grip shifters with a Nashbar basic mountain crank mounted to a brand new Shimano UN-BB54 square taper. The chainline is 47.5mm measured at the middle chainring but I still have a lot of issues getting the bike to shift chainrings in particular. The last straw really was an inability to get into the granny ring climbing up a hill when I really needed it.

Yard sales, thriftstores, pawnshops are all good sources other than CL. Most of the time one can get a pretty good bike for the money. Paid 50.00 at a pawn shop for a rigid Fuji mtb. It needed a set-up that I did myself. The tires were shot, but I found a Roadmaster w/good tires in a dumpster. I used those tires for 2 years. Then I got some street tires. All in all I rode that bike 5 years. Replaced the wheelset, chain and cassette during the years of it's use. Money well spent.

OP, I hear what you're saying about navigating the used bike world. I think there's a lot of good tips in here and you can find a good deal. That doesn't mean it will be fun or you feel like doing it.

Here's another option: this one or others at BikeDirect. $250 delivered for a new bike. Hardly a great bike but less of a BSO / POS than you might find for the price new. You'll need to know what size works for you and be able to do the fitting and some minor assembly yourself (unpack, attach stem, front wheel, pedals, etc) or you'll be in to a shop / friend for ~$50 or beer. It will otherwise be set up better than a big box retailer.

Or best of luck competing with the other bargain hunters. And happy trails this winter on whatever you find.