The first time I tried getting into the OSR, I found some very helpful people willing to explain things to me with patience. This was very nice! But I felt rather out of place, because I was the youngest person in the community (by at least a decade), and it was very mono-gendered. It was a decent place for me to learn a little, but not to play in. It also didn't help that it was almost only people from the USA, so timezones didn't line up at all.
The second time I tried getting into the OSR, I decided to read up on things myself first, so that I wouldn't be going in blind. This time, I instead found a few OSR creators to also espouse political views or having done things in their personal lives that I found very objectionable. I know that's not the case for the OSR movement/community as a whole, but in some of the Discord servers that I joined during this time, I saw others voice support for these creators or their views.
More recently, I've begun to try for a third time, but now just consuming OSR-related media more slowly, by following some creators on YouTube and Twitter. That's been a very good experience so far. I know OSR lives a lot in blogs, but I find blogs on personal websites hard to follow, remember to check, and generally reading long stretches of text online/on PC is a problem for me.
A community's first impression counts for a lot in it looking approachable! A statement on general principles they stand for or against helps separate the good from the bad. Code of Conduct type things need to be very clear and well-enforced. Beyond that, for individual people, just generally being welcoming and kind to all, open to other ways of gaming and how people talk about that, willing to answer questions but also willing to listen--that all helps a lot! I never was able to find those first groups of people I interacted with again, but they were an excellent example. I just felt like outside of games I shared no common ground with them, which makes forming friendships harder.
I have come across some OSR fans that seemed rather anti-other styles of gaming, which turned me off communities that had such vocal proponents, but overall the OSR folx I've talked to just love the DIY feel of a lot of the movement and seem to be accepting of other styles of gaming too. And that is very nice to see.