My recommendation would be to get approved as a Landlord, contact the director's office and request that an inspection be completed before a tenant is selected (sometimes they will do this as long as you select a tenant within 14 days - which you want anyways), and have an online application and screening resource in place.  

There is a cumbersome way to do it on paper forms, but you should not.The only sensible way is to submit your 1099s to the IRS online, however not directly with the IRS.

Quote from @Brandon Foster: Hello Ryan,STR is do able in the north county area but there are a lot of rules and regulations.The city of Oceanside right now will not allow anything STR unless it’s west of pacific coast hwy.This is changing a lot too so you need to be aware of that in your plans.Carlsbad is super strict too but there are some condos that are still available to do STR in.Medium term rentals are as safer bet but way less profitable.

There are a ton of online resources.You could also look at the Arcade1 cabinets as well as the Gamer Legends stuff.

I do SMS, cold call, mail, online, wholesalers, etc.

Networking, local meetups, door knocking, mailers, wholesalers, online forums specific to your area of interest.  

You're best bet is to call a few brokers local to the area and see what they can come up with.It's definitely going to be a surplus or excess carrier that will do it and the premiums will be high. 

I’d love to hear about the crime rates or any other issues (which we cannot guess from the online stats), and how easy or hard it is to find reliable tenants and property management companies.

I’m not a betting man.

I'm betting he'd drive to that area.