reply to u/Pope_Shady at https://old.reddit.com/r/typewriters/comments/1iwrlij/highest_price_youd_spend/
Generally my cap for typewriter purchases is in the $20-35 range. Most of my favorite machines (the standards) were acquired for $5-10 and they're so much better than the portables. At these prices I'm not too worried about the level of work required. I regularly spend 3-4 times more money on a full reel of bulk typewriter ribbon than I do on a typical typewriter.
A few of my more expensive acquisitions:
* I went as high as $100 on a machine (including shipping) to get a Royal Quiet De Luxe with a Vogue typeface that turned out to be in about as stunning a condition as one could hope for.
* I went to $130 on an Olympia SM3 in part for it's Congress elite typeface as well as an uncommon set of mathematical characters. I'm sure I could have gotten it for significantly less, but wanted to help out the seller and it was in solid condition except for worn bushings.
* I also went to around $150 for an (uncommon in the US) early 30's Orga Privat 5 that was in solid shape. I've yet to run into another Orga in the wild in the US since.
It also bears saying that I don't mind buying "barn machines" as a large portion of the fun in collecting for me is cleaning, adjusting, and restoring them to full functionality. I've been dissapointed once to have bought a Remington Quiet-Riter once for $10 only to discover it was in near mint condition and didn't need any work at all.
I am at the point where I'm going to need to start selling machines, work at a local shop, or start my own shop if I'm going to keep up with the "hobby" and maintain a sane spouse simultaneously. If I didn't enjoy wrenching on machines so much, I would definitely be buying them from local shops for significantly more money, and I'd probably have far fewer.
It's not talked about in great length in some typewriter collector spaces, but I think some of the general pricing "game", beyond just getting a "deal", is the answer to the questions: "What am I into this space for anyway? What makes it fun and interesting?" If you don't have the time, talent, tools, or inclination to do your own cleaning and restoration work, then paying $300-$600 for a nice machine in exceptional clean/restored condition from a shop is a totally valid choice and shouldn't be dismissed. Some are in it for the discussions of typewriters. Some are in it for the bargain hunt. Some just want to write. Some want rare gems. Some want common machines from famous writers. Others just want one "good" machine while others want all the machines. It's a multi-faceted space.