By accident, I discovered through discussions with my oldest daughter who was home over the holidays from University that there is quite a market for renting out places to college students.

Your scenario is a Personal policy issue (when rentals are tied to an investors home and auto) not when you have a Commercial policy.Commercial policies work off the ratio of paid losses to paid premium. 

At one point my SO and I were saving about 60% of our income, mainly through auto-investment in Betterment on a weekly basis.I've decided that since I now have more time on my hands I want to withdraw a portion of my Betterment investment and use it for my first rental property.

@Matt HolmerWe use the commercial grade concrete paint that you would see in auto-repair garages, warehouses, etc.  

I was in an accident years ago and I firmly believe that if I wasnt in a truck at the time, I wouldnt be here... 

.- If all else fails or if the auto is high value, I'd pay the $150 to have it towed to the end of the driveway and backcharge the tenant.

Most just want to setup a search criteria -- that any buyer can do themselves -- for bed/bath/size/price/zip and auto FW results).So unless by "San Diego" you count BFE burbs to the east or north, it's pretty bleak here for that type of thing. 

But, setting up auto-debiting from one of your accounts is. 

@Fred EnghA broker would never "by accident" make their cap rate too low, right?

Automatic deposit of rent payments followed by auto draft mortgage payments with text alerts to my phone.