It will be an STR with no personal use  Background: high income W2 job, no primary home (ADU on family's land property, happy twith this) so can't get umbrella policy with most insurers as they want auto and homeowners for primary home before offering umbrella  Quotes from foremost and proper.

Look into DSCR loans, which use rental income for qualification, allowing you to scale without relying on personal income.

I know little about owner financing, and to be honest, if I take on a 300k house payment (or even 250k for that matter), I would struggle to make the payment if I had a prolonged vacancy due to my current W2 income. 

Every day I mark how many calls to leads I made, how many people I contacted (and was it email, call, text) from my database/past clients....how many social media posts I answered or made, etc.I don't know if that's automating, but every week I can quickly see how much of each money generating thing I did.Do you use Google Calendar? 

With two rentals, you might consider QuickBooks Online Plus, which allows you to track income and expenses by class codes (ideal for separating each property’s income & expenses to assess profitability by property).

So I  have a income of around 15k from the business.

Its pretty awesome (BTW, I am not affiliated with FUB, just a passionate users)You can capture all the homeowner demographics along with associated relationships and information - pictures, files, emails, notes, calls, text, etc.You can have a team number(s) at no addition costs (we use it to lead generate for different states and can be configured to round-robin. 

Is your Adjusted Gross Income over $150k where you can't reduce your income with rental losses?

My original plan was to find a 4 plex in california buy using fha loan, move out after the first year and generate cash flow and appreciation, but after looking at properties it became clear to me that’s not possible with todays market and interest rates.

What do I need to do to generate leads and close deals?