Hello and welcome to LessWrong!
First, let me say I enjoyed your post. Straight to your questions, outlined your thoughts and reasons, and actively engaged me during the reading. With respect to that, I'll jump right to the links I gathered from around LW that might interest you (note: I'm not an LW deep-diver and there is much I missed. These are surface level and low-hanging fruit to start with):
A Human's Guide to Words - This is a collection of posts concerning words, our attempts to communicate and rely information, and these concepts connect with objective reality. It's a discussion of (among other things) breaking down what we say to get at what we mean and exploring unknown or unacknowledge or misunderstood implications of our words.
Metaethics - This collection is concerned with ethics and morals as well as what "should" and "right" mean. I think it will be very relevant to your exploration of "deserve."
Evolutionary Psychology - Link is to a wiki article, but look at the bottom for the posts. This discussion of evolutionary psychology may be helpful in its attempts to break down and explore the evolutionary origins of the human mind and how that can lead to "black box" concepts (like "justice") whose origins become very difficult for humans to explore.
I'd also suggest the collection of posts titled Map and Territory for some general ideas regarding exploring hard concepts and breaking difficult questions down. And as a good introduction to LW writing material.
I hope these prove to be useful readings. I found your admission to being less well-read than may seem fit for an LWer to be quite refreshing. How well-read you are, though, is less important than how realistic you are, how creative you can be, how willing to face questions and find answers you are. I look forward to seeing what you contribute.
Glad to have you join us! I hope to see you in the conversation.
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* Normal_Anomaly
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A note for theists: you will find the Less Wrong community to be predominantly atheist, though not completely so, and most of us are genuinely respectful of religious people who keep the usual community norms. It's worth saying that we might think religion is off-topic in some places where you think it's on-topic, so be thoughtful about where and how you start explicitly talking about it; some of us are happy to talk about religion, some of us aren't interested. Bear in mind that many of us really, truly have given full consideration to theistic claims and found them to be false, so starting with the most common arguments is pretty likely just to annoy people. Anyhow, it's absolutely OK to mention that you're religious in your welcome post and to invite a discussion there.
A list of some posts that are pretty awesome
I recommend the major sequences to everybody, but I realize how daunting they look at first. So for purposes of immediate gratification, the following posts are particularly interesting/illuminating/provocative and don't require any previous reading:
More suggestions are welcome! Or just check out the top-rated posts from the history of Less Wrong. Most posts at +50 or more are well worth your time.
Welcome to Less Wrong, and we look forward to hearing from you throughout the site!
Once a post gets over 500 comments, the site stops showing them all by default. If this post has 500 comments and you have 20 karma, please do start the next welcome post; a new post is a good perennial way to encourage newcomers and lurkers to introduce themselves. (Step-by-step, foolproof instructions here; takes <180seconds.)
If there's anything I should add or update on this post (especially broken links), please send me a private message—I may not notice a comment on the post.
Finally, a big thank you to everyone that helped write this post via its predecessors!