Huh. You make a good case for Portland which ameliorates some of my recent negativity: typewriters, civil unrest, typewriters, civil unrest.... I might give the upper hand to typewriters, any place can have an little unrest, after all?

New York City is, surprisingly, not a typewriter town. A few years ago I searched and did not see one typewriter centric club, there are only a few repair shops in the metropolis and not much of a market for typewriters. Hobbies in general seem beneath or above or laterally displaced from the interests of most New Yorkers, working all the time and being angry and such. I'm on the island from time to time, and encouraged that in any line of storefronts which look like a piece of a traditional town, there is often an actual hobby store. Maybe Nassau County is a typewriter town.

Portland sounds indeed like a typewriter town. As far as I know, we do not have such place in the Netherlands. There are a handful of vintage shops scattered over the country  that also sell typewriters. I think the biggest source of typewriters is the Dutch online marketplace, marktplaats.nl

I would consider the greater Toronto area to be a typewriter town. Aside from Toronto being the largest city in the country, Toronto was once home to a number of typewriter manufacturers. The Canadian brand Commodore was assembled here. Underwood, Olympia and I think Remington had factories here too. Royal and Smith-Corona had factories in Montreal, so American brands had a strong presence in the area.

The used market is fairly large and diverse, but it has been destroyed in recent years by parasitic middlemen. When I started collecting, a $50 typewriter was considered to be quite expensive. I still consider that a lot for any make or model, but now it's common to see machines advertised at $500 or more. The only reason for these ridiculous prices are the aforementioned middlemen who buy as many inexpensive machines as they can get their hands on, give them a cursory cleaning, and sell them for ten times what they paid for them.

The latest trend for these typewriter flippers is to give the machines gaudy paint jobs, presumably to make them seem more rare to uninformed buyers (I once argued at length with someone that the Royal FP he wanted to buy for an obscene price was not originally painted shiny gold by the factory).

There are also a great number of antique shops in the city, and a few good antique markets, all of which makes finding a typewriter a fairly simple task. 

There were a number of repair shops, but they've been slowly disappearing and I can only think of three that are still around. I wouldn't entertain using two of them. The third is the only reputable shop, but it's run by a octogenarian and I can't imagine his brick and mortar business will be around much longer.

There are of course a number of guys in the area who like to advertise themselves as typewriter repairmen, but they're really just shade tree handymen who think that their tinkering skills are sufficient qualifications for the job.

There's not much of a typewriter culture though in Toronto. At least not one that I'm aware of. There were attempts in the past at organized type-ins, but they were run by a fledgling typewriter business that was trying to lure new customers. 

I've officially stopped collecting, and rarely look at what's available in the area, but if I do buy a machine now it's most likely from another local collector. My latest purchase was a couple of weeks ago, an Adler Tippa that I got from Valiant (another member here). He's constantly buying and selling machines, and is one of those guys who finds machines at the curb...

Philadelphia may be trying to become a typewriter town. Before the pandemic it was more on its way, everything seems stagnated right now.
Phil Forrest

Guth, thanks for the kind words.

I don't think a direct comparison can be made between typewriter and camera/turntable pricing simply because of the difference in demand for those items.

Like you, I was a regular user of 35 mm cameras and used my turntables daily when they were the norm. Unfortunately, I sold most of my 35 mm gear years ago when I made the switch to digital, and I deeply regret that now given how little money I got for it at the time (I did keep a Zeiss Contaflex and a Rollei, but more for sentimental reasons). I never sold my audio equipment, probably because it was the only way I could still listen to my LP collection. 

As we know, LPs have made a huge comeback, and as a result there's a great demand for vinyl equipment. New turntables are still being produced, as are LPs, but this only satiates some of that demand. It's an active market, which partially explains why used LP pricing is relatively high.

Photography using film also seems to be enjoying a resurgence of sorts, although it's not nearly as large the current vinyl revival. Photography is a far more popular hobby than typewriter collecting and the demand for vintage camera gear will likely always outpace the demand/interest in typewriters.

I can't comment on the influence young people have on vinyl and film sales, but they are not the sole driving force behind typewriter sales - at least not in my area. I've been very attentive to the demographics of typewriter buyers and have found that it's just as likely that a middle-aged person wanting to revisit their youth will buy a typewriter than some millennial who actually has an interest in writing. There's even a good likelihood that a good-looking vintage machine will be purchased as an ornament for a bookshelf.

The supply of typewriters in my area has not seemed to wane at all in the past decade, there doesn't appear to be any risk of demand outstripping supply, and yet the pricing has steadily increased itself to ridiculous levels. In fact, if the local collectors that I know were to list all of their machines right now there would be a real glut of typewriters available to potential buyers.

I believe the changes I've seen in typewriter pricing are the result of a monkey-see, monkey-do situation. A middleman buys a machine for $30, spends an hour or so cleaning it and making sure it works reasonably well (sometimes they don't even do that), and then lists it online for $400. Some are slimy enough to claim that it's RARE and that it has been REFURBISHED. Very few typewriters are actually rare - and a spit polish is not a refurbishment.

If they've given it a rattle can paintjob, which I see is the latest trend, then they'll ask $550+ for the ultra-rare machine with its desirable colour.

The direct effect of these online resellers is evident in the postings of those who found a typewriter in Grandma's closet and just want to get rid of it. They have no idea what they've got, so they go online to figure out what it's worth and see the middlemen pricing, and assume their typewriter has to be worth that much too. They list their machine for a few bucks less - after all, it hasn't been refurbished and they're not sure about how rare it is.

What used to be the norm - a person selling a family typewriter for $30 just to get rid of it - is now the exception. And when such machines do get listed, they are grabbed - sometimes within minutes - by the middlemen for inventory.

Who is buying these machines at those crazy prices? Well, I know of one collector who has more money than sense, and have marveled at what he will spend of average typewriters. There are plenty of one-time buyers too who just don't know any better - and those who might know better but are simply impatient and willing to overspend to get something now.

I am of course talking about my local market. Buyers who don't live in a typewriter town have fewer options and might be more desperate, and more likely to pay too much.

The bottom line is simple: As long as there are people out there willing to pay $650 for a $30 '50s Smith-Corona Sterling with a $10 paint job, there will be people willing to sell them - and prices will remain high. If I had any sense I'd be selling off the bulk of my collection now, but no one has ever accused me of being that smart.