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This advice assumes you’re in the U.S., so apologies if it isn’t all applicable:

Buying in person is the best option. Since it’s your first typewriter, your concerns should be availability and price, not more subjective things like “feel,” “action,” etc.

A note on price: As with anything, the right price is the price you’re comfortable paying. That said, it’s worth keeping in mind that typewriter pricing is often very disconnected from market pricing. As it’s become a more popular hobby, it’s become saturated with people trying to turn a profit reselling things they found. You’ll see people listing relatively common machines for many multiples of what they’re worth (say, a machine worth $100 being sold for $500).

Unless you’re absolutely in love with a specific machine, I’d recommend setting your budget to ~$100 and buying the first one that satisfies these conditions:

1) Does the carriage smoothly run forwards (using the carriage release lever) and backwards. 2) Does each key swing freely when depressed and immediately fall back when released? 3) Does pressing each key advance the carriage exactly one step? 4) Is there no rust whatsoever?

If the answer to any of these questions is “no,” move on. It’s not worth investing in a broken machine (but a lot of first timers mistakenly do).

Older manual typewriters come in two flavors: standard and portable. Think of it like desktops versus laptops. Standards weigh a ton and take up more space, but are generally cheaper and more reliable.

Where to buy in person (in terms of ascending cost): Craigslist > flea markets > thrift stores > antique stores > typewriter repair shops. All but the last one will require some hunting. Antique stores are mostly likely to have wildly inflated prices. Usually this is because the seller “researched” the price by looking it up on Google and seeing an Etsy listing that has been up for years at a price no one would ever pay.

If you just want a machine you know will work and you don’t mind overspending, go to a typewriter shop. Most major cities have one. You’ll pay more than you should have to (think $500-$1000 for some that that could be had for $100-$250), but you’ll get the benefit of having a professionally serviced machine that works.

Online: Don’t do it unless you have to.

If you do buy online, only buy a portable that comes in a case. Never buy a standard (desktop) online, it won’t survive shipping no matter how well it’s packed.

Keep in mind that most sellers do not know anything about typewriters. This means that they don’t necessarily know what a “working” typewriter is. They might think it works because the keys depress, but don’t know that the carriage is broken and isn’t advancing. Look for a description that suggests the seller knows what they’re selling and, if possible, a history of selling typewriters.

Sources: using shopgoodwill.com to buy an unwanted/unpopular machine is your best bet, but there’s no guarantee that it will actually work when it arrives. Same with eBay. Avoid Etsy like the plague. Dedicated typewriter retailers will be as (if not more) overpriced than a typewriter store, but with the added risk of damage during shipping.

A short note on brands: like any hobby, there tends to be a lot of clustering around certain perceived wisdom. This is especially true of typewriters, where there’s a strong Reddit karma farming component where people want to buy and post about the thing that other people post and get likes. Most commonly, you’ll see people suggest: Hermes, Olympia, Smith Corona, and Olivetti. This meming results in the prices for these machines being hugely inflated (this is triply so for Hermes which are also incredibly fragile and often broken). Don’t bother with any of these unless you find one in your original budget. Any number of Underwoods, Royals, Brothers, or ugly 70s machines will do just as well for your first typewriter.