Hello Biking Friends!

I am new to this forum but have been road biking for about 8 months or so.

A few friends and I are planning to ride SF to SD in the late fall. While we have taken weekend rides up to 55 miles in the SD area, we were wondering if the community had any tips on:

1) Routes in SD county to take/train on for the trip.
2) Any middle of the week tips on training for mileage, hills, cross training
3) Sample schedules, routes, that have been useful in the past.
4) Any other bits of wisdom that comes to mind.

We have about 20 weeks to prep for the trip. Thanks in advance!!