Alright so basically I'm looking for a rule of thumb while and singing and playing and how I need to sing vs. what key the song is in.

Ya know like if I have a relatively higher pitched voice I should play in a higher key, or lower key, etc, blah blah blah...

Without getting to technical what is the general rule of thumb there?
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i don't really understand what your asking
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uhh the same key, but possibly different octaves...this is kind of a weird question. i think your trying to ask about pitch...
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Without getting technical, try to sing it in the key it was written in. If that makes it too high for you to sing, play everything a bit lower and sing it in your comfortable range. If that makes it too low for you to sing, do the opposite.

A capo is a useful tool for this.
Find your vocal range, and play in keys and octaves that fit.
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Find your vocal range, and play in keys and octaves that fit.

My best note (standing) is B below middle C. I would want to transpose songs and write songs around B (so A, Bb, B, C, C#), as I will have to resolve to one of these notes and so this note should be relatively easy for me to play.

I dont think it matters what octave you play in. Although some guys reckon that if your melody line is lower than some of the notes in your accompaniment (like chords and so on), than your melody will become ambiguous. Not sure if I agree with that, but keep it in mind (I'm actually pretty sure I dont, but make up your own opinion).