#2
I think it sounds good, your equipment doesn't seem that crappy (I don't think most people here have pro gear anyway). Your singing is mostly fine (certainly nothing you need to hate) Though maybe you could probably make it sound better with a bit of reverb and fiddling with the EQ.
#4
Both. I'd experiment with different types of reverb. Lately I've been using room reverb for my guitar and most instruments, while fiddling with plate reverb on vocals, finding that works pretty well. But you'll have to see what works for your voice. Having said that, I do like your song. With a bit of work on the production, it'd be really good imho.