I'll save you the trouble: "Scour Craigslist every hour for days on end until a great deal pops up on an old 90s steel road bike from a reputable manufacturer, buy any replacement components, then teach yourself how to completely tear down and rebuild a bike." or "Save your money and get something nicer because those are crappy bikes and you'll spend more money fixing them or replacing parts than if you'd just bought a better bike in the first place."

I understand why these are the most common responses. But let's just get it out of the way and say that I'm stubborn, cheap, and not an avid rider. I've made do on a $100 used GT mountain bike for the past 8 years and it's done everything I've wanted it to...until I went on my first (metric) century ride this past weekend and realized that it doesn't fit and it certainly isn't suited for long road rides. So I'm looking to "upgrade" to another cheap bike that will let me putter around town on the roads and greenways - mostly 10-15 mile roundtrip rides - and let me to the occasional century without the pain. Maybe in another 8 years I'll consider a better bike, but in the meantime, I would sincerely appreciate your opinion on which of these bikes is "best", with the acknowledgement that they're both horrible and no self-respecting cyclist would ride them. I'm not much of a cyclist and I have no self-respect, so it's not an issue for me.

Schwinn Solara for $203 (after tax and REDcard discount) from Target: target.com/p/A-14897764
Vilano R2 for $209 from Amazon: amazon.com/dp/B01FIKABTQ

Both have the Shimano Tourney groupset (I think that's the right word, sorry if it's not) and A050 thumb shifters. All are 6061 aluminum (with steel forks, I believe), have drop bars, and come with side-pull caliper brakes. The differences appear minor, but I'm wondering if they matter and if so, how much. They're both cheap, but if one stands above the others as slightly less crappy, I want that one.

The Schwinn is a 14-speed (2x7), while the Vilano has a 21-speed triple crankset. 21 seems better for climbing hills, but maybe not? I certainly don't use all 21 gears on my mountain bike when I'm on the road. The Vilano has a dual-pivot side-pull brakes, while the Schwinn is single-pivot. Dual is better, from my understanding. The Vilano has quick-release on both the front and back wheels; the Schwinn only has quick-release on the front.

Past that, the remaining advantage of the Schwinn is that I can easily return it within 120 days, no muss, no fuss. It also comes with a "lifetime warranty", for whatever that's worth on a department store bike. I'd say it's a bonus that the store assembles it, but I suspect that I'd be better off having them ship it to me in a box to do myself than trust a store employee to do it.

So...Schwinn or Vilano? Which is the lesser of two poor choices? Or is there a significantly less poor choice around the $250 price point (new bike, not used, and no Craigslist)? If there's a bike that's twice as good (all things being relative) for $50 more, I'll consider it.

PS. sorry for the lack of links, I can't post proper URLs, yet.

The ability to return it to the place of purchase is a big plus. Single or dual pivot brakes is a non issue. I would lean toward the Schwinn, bought locally. Qr wheels are easy to come by, should you decide you want one on the back, plus non qr is more difficult to steal.
My two cents
Even after it is assembled at the place of purchase, it should be checked for tightness of all bolts and nuts, especially around the steering area and the seat and pedals.

You might also check your lbs, if there is one, for used bikes in that price range.

Although, like you mentioned, I would much more advise grabbing a lightly used bike off craigslist. You would probably be better suited getting a bike from here (Save up to 60% off Road Bikes, Free Ship 48, Schwinn, GT, Kestrel, Fuji, Motobecane and more Road bikes. Authorized dealer for Schwinn, GT, Kestrel, Fuji, Motobecane, Mercier, Gravity, Dawes road bikes. Shimano Carbon Road Bikes, Titanium Road Bikes,) they have multiple options in your price range that I would say are better than the two you posted and gives you the option of different sizes.

Thank you for the feedback! Good to know the brakes aren't significantly different and that there isn't a huge advantage to QR on the back tire (for me). What about the 14 vs 21 speed setup? Is one significantly advantageous over the other?

I would definitely go over the bike carefully after they assemble it; I'm a professional bike mechanic, compliments of that one YouTube video that I watched

I checked the stores around me and to my surprise, the ones that did carry used bikes didn't have a great selection. I used this frame sizer (ebicycles.com/bicycle-tools/frame-sizer/road-bike) and it said I should look at something around 57cm. I wasn't actually measured at any of the stores, but the consensus was that they didn't have any bikes big enough for me within my price range. Truly, I did look at my LBS and Craigslist before deciding to go with a new, low-end bike.

A friend of mind mentioned this site in passing and I checked it out. The only two that are in my price range (well, $250), are the Mercier Galaxy SC1 LTD (bikesdirect.com/products/mercier/galaxy_al_xi_sc1-holiday.htm) and Gravity Swift7 (bikesdirect.com/products/gravity/swift-flatbar-hybrid-xiv.htm). The former has stem shifters (something I tried and didn't like, but I didn't give it much of a chance) and the latter has a flat bar. If you have a moment, I'd sincerely appreciate you eyeballing them and telling me if they do seem better than either of the options I listed.

OP- I had a triple on my Denali (similar to your Vilano option, I believe) in its original incarnation. I didn't need it for my location as there are no hills of any consequence, so unless your riding terrain requires it, I wouldn't be too fussed over that option. I would also opt for a local purchase for the ease of returns/warranty issues, unless you really are comfortable assembling something by yourself and have the time to do so. I'd vote for the Schwinn or the Mercier for your scenario, personally. And the Mercier in the above post looks like a better deal. I also had stem shifters for a while and once you get used to them, they're not bad. Easier to work with than grip shifters, anyway.

The Denali was on my list for a while! I didn't care for the twist shifters, either. I had them on the bike prior to my current mountain bike (which has trigger shifters) and it's probably one of the biggest reasons I took the Denali off my list.

I do have the time and willingness to put a bike together. We do have a fair amount of hills in the area. The century this past weekend had 2000 feet of elevation gain. Not crazy, but hardly flat. And so in that case...would the 21 gears make that much of a difference over 14?

Yes, the extra chainring would make a big difference if it is hilly.

And I, personally, would reject any bike with gripshift. I don't mind stem shifters either.

Don't know if you can go another $100, but if so, the Windsor Wellington at Bikes Direct has everything you're looking for. I rode a group ride with a guy on an amazon.com bike, and it didn't impress me one bit. Good luck with whatever you decide.

Hard to say without any detailed information, but at a glance, the Vilano R2 looks like a considerably better machine.

With only seven speeds in back, two chainrings is pushing it, especially since many arrangements lack reasonable shift patterns to make up for low ratio counts.

Dual-pivot calipers are tighter and easier to adjust than single-pivot. The only reason a bike should ever use single-pivot calipers is for aesthetics on a steel frame with narrow tubing, and only then if the brake is silver.

Is that a bolt-on axle on the Schwinn? If so, you'll have to carry a wrench to fix a flat; that's fine for the velodrome, but kind of silly on the road.

What's going on with the Schwinn's stem? That's hideous.

I can go another $100, I just need a compelling reason to do it. There are four Wellingtons on the site. Do you mean the 1.0 for $260 (bikesdirect.com/products/windsor/wellington1-xv.htm), the 2.0 for $300 (bikesdirect.com/products/windsor/wellington2-xv.htm), or the 3.0 for $350 (bikesdirect.com/products/windsor/wellington3-xv.htm)?

And what makes them better? This is where my ignorance is especially obvious. If you're referring to the 2.0, it looks to have the same groupset as the Vilano (Shimano FD-A073 / RD-A070D / SL-A050). It's still aluminum and has a steel fork (though it's chromoly instead of hi-ten).

All good to know, thanks for the info! Is it a bolt-on if it's not a QR? If so, then yes, it's a bolt-on.

On the Windsor 2.0 seedsbelize mentioned above, the bike has a CroMoly fork, which weighs less than the Hi-ten steel fork of your other options, and thus also affects the price. It's also evidently got braze-ons for a rear rack, double water bottle mounts, and perhaps (?) slightly better wheels. At this price point, much as (I imagine) at the other end of the spectrum, you are paying more for very slight gains- you just have to be willing to compromise a lot more on this end. I commend your ability to ride a century on a mountain bike like that, and will also echo seedbelize and wish you the very best of luck on your purchase. And congratulations on whatever you end up getting. FWIW, I've found I really enjoy working on bikes, and it brings another level of enjoyment to this hobby.

Okay, let's say I decide to go the used bike route. Two options near me are:

2008 Fuji Cross Comp for $300: bikepedia.com/QuickBike/BikeSpecs.aspx?Year=2008&Brand=Fuji&Model=Cross%20Comp&Type=bike
1996 Raleigh R-500 for $250: bikepedia.com/QuickBike/BikeSpecs.aspx?year=1996&brand=Raleigh&model=R500

According to the sellers, everything is stock on both. The Raleigh is being sold by a guy with a "shop" (he's retired and has been fixing up bikes for a couple of years, sells them out of a storage unit), but he seems like he knows what he's talking about. The Fuji is just the original owner. Thoughts?

The Fuji is a fantastic deal, so long as it fits.