I do take on occasional low price commissions for indi/non-professionals when I have a gap in my portfolio I'd like to address. Usually one-off pieces, though, not lengthy projects that would interfere with my ability to actually make a living, a necessity as a full time freelancer. So it is possible to get map work for lower than $300. It takes some fishing, and meeting the right person at the right time. That said, the kind of detailed city map like you referred is extremely time consuming to create, and depending on the artist, may be a solid 50-60 hour project.

There are all kinds of fun resources for beginning map artists. One I'd refer you to is this fun city/town generator. https://watabou.itch.io/medieval-fantasy-city-generator It might serve as a good jumping off base for you to get those small towns labeled, for free. If you fiddle with the settings, it has the option to generate labels, and houses versus blocks, change the colors, etc. Definitely a lot of potential for a base for a town. Then you can save the money you otherwise would have spent on these small town maps.

In the end, you will not be young forever, and you will probably not be broke forever, and the maps you draw, if you choose to start drawing them, will not be ugly forever. Everyone starts with art that makes them go "ehh this isn't very good", but then you take it and do it over and over again.

Yeah, there's some amazing professional cartographers here with jaw-dropping art at spendy price points. They can charge that due to their extensive knowledge and experience. But I bet every single one of us started mapping the same way: a pencil and a piece of paper and a dream. Asking questions is free, and even lurking and reading can gain you tons of information. Skulking around this forum will get you map brushes and resources, tutorials, other people's WIPs and questions and answers... don't worry. No one here wants you to leave if you're hanging around to learn.