Some answers........though I'm not sure they will be satisfactory......
1) The portfolio feature of X_DEV needs to be.....upgraded/enhanced to perform more accurate accounting for dividends and/or distributions. Currently you can input them manually by choosing the "add stock" icon in the portfolio manager, but you will have to update the buy sell activity as well.
2 and 3) Optimization algorithms would be great, but beyond my grasp, and I'm not sure they would work as intended. I think the human element needs to be maintained for reasons of .....flexibility. Each trader trades differently according to risk profile, time frame, style, etc. A mechanical optimization process couldn't fit everyone's particular needs, but I'd like to explore the possibilities. Are you a programmer?