Bikes benefit a lot from pneumatic tyres, pressure pumps, smooth asphalt (not cobbles), precision engineering of chains, chemistry of oils and lubricants, rust-proof steel, rubber brake pads with compounds that last long enough and resist rain, spring steel for suspension, cables that don't stretch. Without those things you get a wooden boneshaker hobby-horse, large, heavy, energy inefficient, incovenient: https://duckduckgo.com/?q=hobby+horse+victorian+bike&t=ffab&...
(And internal combustion engines; how are you going to distribute them around the Roman Empire by the tens of millions without trucks or ships?)
And now of course some of the most prestigious races in the professional cycling world are across predominantly cobbled roads as a form of torture for those racing.
To expand on one of those things - bike chains get slightly longer as they wear out. Once it's about 1% longer than it started, it looks about the same as it always did, but it's starting to damage the drivechain and you need to replace it. An ancient Roman blacksmith has no hope of making a chain with anything like that level of precision.
I believe you only have this problem if your bike has gears based on a set of sprockets (different size chainwheels and a derailleur to move the chain from one to the other).
In Europe (Holland in particular), people ride single gear city bikes (or internally geared hubs) for decades without replacing chains or cogs. When you only have one chainring and one cog, they wear along with the chain, and it takes a very very long time to encounter problems.
It's when you have the sprocket cluster with multiple cogs that are not all wearing equally, that you get problems. Or often the problem on geared bikes doesn't appear until you replace your worn chain and the new chain no longer meshes well with the cogs worn to match the old chain.
Nope, with single speed/hub gears chain wear is still a problem, it's just that they're less sensitive to it and there's fewer parts to replace. When the chain gets longer it gets loose, but it has to be very loose indeed to fall off or skip on a single speed. With a derailleur setup there's a tension arm with a weak spring so when the chain wants to skip that tension arm lets it. Derailleur setups commonly have some cogs with fewer teeth than single speeds so the problem is more obvious. Also, often derailleur cogs are aluminium while single speed ones are steel (not always!).
Typically a safety bike will get through 3-5 chains before needing to replace the rear cog, and many more before replacing the chainring(s). But Pinion gearboxes in the bottom bracket often run small chainrings that are similar in size to the rear cog, and I suspect they need to replace both rather than just the rear one.
I ride a bicycle with a hub gear as my main form of transport. About two years ago, I noticed the sprocket (rear cog) was getting very worn, so I removed it so I could reverse it and let it wear on the other side of the teeth (standard procedure for this sprocket to extend the wear life). But I accidentally put it back the same way as before and didn't notice until recently when I changed the hub oil. I had no problems with the chain skipping, despite the heavy sprocket wear (although it's now worn to the point that I no longer feel comfortable letting it wear on the other side of the teeth, so I'll have to buy a new sprocket). But you are correct that the chain wears more than the sprocket; I've already replaced the chain a few times.
Wouldn't the chain still need to be quite intricate and pretty hard to make even then? Though now that I think about it, you could probably make it in a way similar to chainmail, since tight tolerances aren't actually that crucial (the results would suck, but only compared to modern bikes). Though the other parts might be just as hard to make and especially to fit together (the bearings, the gearing for the chains...)
Bronze bushes work for bearings (still needs a lathe/ but not ball bearings). Chains can be belts of horsehair (or any civilisation with wire, tube and sheet metal can make a modern chain) or a treadle works okay. Spokes can be wooden.
The main limiting factor is probably the pnuematic tyre and smooth roads.
Chains don't stretch, they wear down. When measuring a chain, you measure the distance between links to see how much material has worn away. The links don't actually get longer from stretching.
You don't have to use chains though, you can have pedals on the front wheel, like the original bikes(velocipedes), or not pedal at all, just push yourself on the ground (balance bicycles)
Penny farthing bikes are death traps. Bikes that have similarly sized wheels with pedals on the front wheel aren't practical enough to be better than walking. Bikes without pedals are also not practical.
They were both more efficient than walking. Humans will put up with death traps if it means more efficiency in transportation (just look at car fatalities). The only reason they didn't took off faster was the lack of roads. And by the time we had tarmac roads bikes already evolved to have chains and read drive.
Watch a kid on a balance bike and tell me how it's not practical, lol. A 4 year old can bike around a whole park in seconds.
The key invention that made them possible was ball bearings. This is why the modern bicycle and the modern car were invented within a year or two of each other.
Yeah. Surfing is a great example of a Stone Age sport that has been radically changed by Space Age technology. Koa wood gets you a longboard that is hard to steer and can only surf long smooth waves. The modern surfboard is very much born out of California's aviation industry and its fixation on light, strong materials and aerodynamics. Surfing Pipeline is only possible with modern plastics, fins and shaping.
Well, I've got a bike from the 30s and it's perfectly fine for everyday riding. While I agree that most of those things you listed are valuable and convenient, good enough is often just good enough. Like I've got no use for any cables and I don't need precision engineered chains.
(And internal combustion engines; how are you going to distribute them around the Roman Empire by the tens of millions without trucks or ships?)