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I designed a couple small (approx 1" x 5" and 1/2" x 2") single-sided boards to mount components and wires to clean up a microcontroller project. I cut 1 of each on my cnc machine and they work, but since I am still working out the kinks it did take a bunch of extra hand work at the end to clean up the traces. Have had a few people reach out to me for kit builds and thought it might make time/reliability/cost sense to have a small run fabbed. I read through some threads here for vendors and had a look at pcbway.com but they are asking for a ton of info that I don't know about. Any tips on best way to approach this?

Group buy on Oshpark that I've been a part of was smooth. Eatyourguitar has posted about his experiences having his stuff made in previous threads.. I can't remember where.. I'll go in on an Oshpark order any time dude

That's all I know. Sorry

Boards from Oshpark are good quality, and you can order a small number without it being crazy expensive. For more than 10 boards though I really recommend Elecrow.

Both require you to have layer files for your board. Learning Kicad is a good way to do this. It's free software, and it's more than competent enough to do multi-layer boards, let alone single side.

PCBway is great. do that. don't email them. I think that is your problem. you just gotta go in like a jedi. you have your gerbers all perfect and you give it to them in a format that they like. if there are no questionable or ambiguous designations in your tool paths that would make no sense or damage the machine then you will never get an email asking you to change or approve the design. if your design just works. then your fab just works on it. if you want me to make gerbers for you I can do that for a fee. or you can risk it and get a set of bad boards as an expensive learning experience. this is how I learned, by making iterative mistakes and paying $20 each time. I paid dues for my education.