Yes. I agree it is a very tall order to bridge the blackboard with the real world. All of the things you've mentioned are very real, difficult hurdles to overcome. Mishedges, jumps, and slippage can be brutal. I believe there are some decent ways to address your list, but it's definitely difficult. The higher moments are a puzzle (for me at least), but that's also part of why this game is fun and addicting. I wouldn't want it to be easy or everyone would do it!
Looks like some theorists having good discussion in this thread! "You shouldn't believe everything you read on the Internet" - Abraham Lincoln.