I need help choosing crops

Hi,

I'm in the process of putting together a business plan to get a loan in order to buy my first property.
I'm looking at 50-100acres in Victoria, Australia. Which is zone 9, where I'm looking is between 800-1000mm of water per year.

The intention of the property is to set it out in 2-5 acre blocks with a perennial support system bordering the blocks. This would include bees.
Each block will be set out in a traditional mono-culture layout intended for mechanized harvest.

I have two questions-:

1) In order to minimize costs in the short term and long run, I'm trying to ensure the crops I plant will share harvesters. So far I have
   -Nut finger roller
           -Hazelnuts + Truffles (Truffles harvested by hand)
           -Black Walnuts (to be canopy layer in perennial system)
           -Other nuts
   -Umbrella shaker
           -Olives
           -Cherries
    What other crops could I look at that would share harvesters

2) Given I'm setting the farm as perennial mono-culture blocks, how many crops do I need to see a benefit? I have no intention of spray and I want to bring in as little fert as possible by creating my own.