I was wondering about the practice of uploading an incomplete demo and gradually updating it over time till completion and polish. I am aware that some devs do indeed do this but I’m wondering about how it’s perceived as a practice. I don’t want to give the impression that I’m a sloppy dev who uploads unfinished work.

It happens often. An indie dev doesn’t have the resources to publish something only when it’s finished, so it’s very often the case that they upload work in progress and keep updating it.

I would say, uploading a game in early stages, and steadily update it looks more hard working, than uploading a finished product once and never updating it, at least in the Indie scene.

A part of me simply feels impatient and wants to upload something for people to play so I can get as much feedback as possible, but another part wants to build a reputation as a hard working dev that cares about quality.

Nobody will judge you or remember you from one game, especially your first one. You need at least 2-3 successes before people start noticing who you are and your reputation.

I’ve never posted a game to itch.io before and would ideally like to go in armed with knowledge.

Uploading your very first game is a massive step. I would say go for it. The only thing you’d need to keep in mind is to be perfectly clear to potential users that the project is unfinished. There is an option to set the project as “In Development”, but also mention in the description that this is a work in progress.

Hope that helps, good luck and looking forward to seeing your projects around :)

I currently have a page with the listing as 'in-development' but it's not indexed because it's just a store page. Shameless Plug
I could probably do what you say, but I worry that people won't read the dev log and simply just download the demo and think "Wow, this sucks and it's buggy. This dev should go dunk themselves in a volcano." This is why I'm asking. Not sure how friendly the itch.io community is towards demos in progress. I'm still feel the need to bathe after reading some of the comments on Early Access stuff on Steam...

First of all, I'd like to say that your game screenshots look very nice and I'm sure the game will be great.  As far as having a demo and updating it as time goes on, I've done it myself several times.  In fact my newest project (a Visual Novel adaptation of my e-book) is a demo that I'm updating over time.  In different cases, because of how long the finished product will be, you have to have a demo you update over time and that's totally fine.