Is it okay to ask questions that have been answered before? I feel like this teaches the search engine to deal with phrasing better.
If you ask questions that have been answered before, unless you add some kind of value to the question that was not there before, unfortunately, people will almost certainly down vote them because they are duplicates, which are not allowed on this site because we do not want the same discussion to be in the site on multiple questions. Simply changing the phrasing is not enough.
Is there some kind of cushion for newbs? I feel like all my problems with this site boil down to my lack of experience with the search engine.
Unfortunately, no, there is not. People usually just expect new users to understand all of the rules and ask quality questions, even though most people aren't really taught how to ask quality questions in school and to many people, this sort of forum is new.
Also, the search engine can be a bit annoying because it often does not give me the question I want, even if I know it exists, so if you ask duplicate questions when you looked for questions of your type and could not find any, it is understandable, but unfortunately, it will still probably be marked as duplicate if people find a similar question, even if that's not your fault.
Often when I ask questions, I can't figure out how to be specific. Only after I've read some answers can I zero in on what I was missing. Is this problematic?
If you have a specific problem but no specific work, try to be very specific with the problem as you can. People usually appreciate users who describe the question in-depth even if they do not show any work. However, people are usually critical of users who post a very short question with no work because they see these as low-quality where answers will only help the user answering that short question instead of fostering a quality question. However, this also isn't necessarily new users' fault because again, people aren't really taught how to ask good questions in school and many people are new to these types of math forums.
In short, just try to be as specific as possible and if you want some kind of hint to your question, but not a full answer, people might give you that hint even if your question is very short. I've seen many answerers leave very small hints on questions, even if the question is very short and those answerers later say that such questions don't deserve a full answer. I think you're more likely to get a useful hint if you ask for it politely even if you don't show any work, but if you're not specific, even if you try your best, unfortunately, you might not get an answer.