Aaron,
The description suggests it could be a Caprifig . Pictures, close-ups, cutaways,.. will definitely help to confirm it or not.
answering your questions...
1- If it is a Caprifig, yes you can get cuttings and root them as you do for all other figs.. but, still assuming it is a good Caprifig, I would rather cut a deal with the lady and ask her permission to prepare 2 or 3 air-layers and you could have small trees in say, 3 months. You would leave these potted air-layers under the mother tree while growing for the full season in other to have them conveniently caprified by April/May 2015.
At that time they certainly show its crop of Profichis (the figs with pollen and wasps) ready to issue the insects by mid June 2015 having in the meantime moved the pots to your orchard.
In other words in June 2015 you could have the benefits of your potted Caprifigs on a good deal of your varieties if not all ...In the fall of 2015 you would moved the trees to the dirt for a permanent position some place of your orchard, depending on the position of your trees, dominant winds, exposure, etc..
2- see above
3- There are many types/varieties of Capri figs,.. dark, black, white, violet, big small, etc.. polleniferous, insectiferous,...
4- Ideally you should have 2 or 3 varieties, issuing insects from mid June up to mid/end July. It seems that San Francisco bay area Caprifigs, issue insects 15 to 20 days later than in San Joaquin valley.
Weather/conditions allowing an insectiferous Caprifig will always issue wasps. It would help to position these wild figs in a somehow protected area, avoiding direct exposure to the sun and wind.
Let's have your pictures.
Good luck
Francisco